Synthesis of 1,3-diphenylurea (N,N’-diphenylurea; carbanilide)

Preparation of 1,3-diphenylurea

Diphenylurea is prepared similarly as 1-phenylurea. Their separation of two substances is based on the fact that diphenylurea is insoluble in boiling water, whereas 1-phenylurea is readily soluble.

Preparation of 1,3-diphenylurea (N,N'-diphenylurea; carbanilide; diphenylurea)

Preparation of 1,3-diphenylurea (N,N’-diphenylurea; carbanilide; diphenylurea)

12 g of aniline hydrochloride and 6 g of urea are dissolved in 50 ml of warm water. The obtained solution is filtered and transferred the clear filtrate to a 250 ml glass flask, fitted with a reflux condenser. The reaction flask is boiled under reflux for 90 minutes and crystals of diphenylurea usually appears after about 30-40 minutes. Occasionally however, the solution remains clear due to supersaturation with the diphenylurea. In such case, a sudden separation of the crystalline diphenylurea will usually occur after vigorous shaking. Also to prevent the reaction mixture from “bumping” constant stirring or few beads of boiling glass are necessary.  After 90 minute of heating the hot solution is quickly filtered through preheated Buchner funnel. The filtered diphenylurea is wahsed twice with hot water, the filtrate is transferred to a beaker which is immersed in ice-water. During the cooling of filtrate the 1-phenylurea separates as colorless needles, which are filtered, washed with water and recrystallize from boiling water. Yield of 1-phenylurea is 2.5-3 g and melts at 147° C. Collected diphenylurea from the original filtration is chemically almost pure. However, it may be purified by crystallization from ethanol. For the filtration of saturated solution is nessesary to preheat the Buchner funnel in order to prevent crystallization of diphenylurea. Diphenylurea forms as fine colorless crystals, with melting point 237° C. The yield of final product is 1-1.5 g.

Practical organic chemistry, by F. G. Mann, 125-126, 1960

IUPAC Name

1,3-diphenylurea

InChI

InChI=1S/C13H12N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)

InChI Key

GWEHVDNNLFDJLR-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)NC(=O)NC2=CC=CC=C2

Depositor-Supplied Synonyms

1,3-Diphenylurea, N,N’-Diphenylurea, CARBANILIDE, Diphenylurea, 102-07-8, s-Diphenylurea, Diphenylcarbamide, Urea, N,N’-diphenyl-, sym-Diphenylurea, Acardite I, N-Phenyl-N’-phenylurea, Acardite, 1,3-Diphenylcarbamide, USAF EK-534, Karbanilid, Urea, 1,3-diphenyl-, Karbanilid [Czech], 1,3-diphenyl-urea, N’N’-Diphenyl urea, N,N’-Difenylmocovina, AD 30, NSC 227401, N,N’-Difenylmocovina [Czech], CCRIS 4634, CHEBI:41320, HSDB 2757, GWEHVDNNLFDJLR-UHFFFAOYSA-N, Urea,3-diphenyl-, EINECS 203-003-7, Urea,N’-diphenyl-, BRN 0782650, WLN: RMVMR, AI3-52320, AQ-917/40171059, F0316-0002, N-phenyl(phenylamino)carboxamide, 2zjf, N, N’-diphenylurea, N,N’-diphenyl urea, Kinome_598, Kinome_627, Spectrum_000422, SpecPlus_000406, Urea-based compound, 7, Spectrum2_001838, Spectrum3_001328, Spectrum4_001561, Spectrum5_000182, DSSTox_CID_5183, UNII-94YD8RMX5B, AC1L1P4D, 94YD8RMX5B, DSSTox_RID_77698, DSSTox_GSID_25183, Oprea1_527136, BSPBio_003055, CBDivE_002165, KBioGR_002082, KBioSS_000902, SPECTRUM211126, KSC175E2F, MLS002207104, DivK1c_006502, SCHEMBL133103, SPBio_001915, 142158_ALDRICH, CHEMBL354676, CTK0H5222, KBio1_001446, KBio2_000902, KBio2_003470, KBio2_006038, KBio3_002275, NSC8485, 3e85, MolPort-000-393-991, ACMC-209800, NSC-8485, Tox21_200068, ANW-14638, CCG-38465, ICCB1_000093, LS-354, NSC227401, SBB058217, STK328350, ZINC12416741, AKOS000312994, DB07496, MCULE-4684667909, NSC-227401, RTR-000546, SDCCGMLS-0066513.P001, VZ36373, NCGC00091344-01, NCGC00091344-02, NCGC00091344-03, NCGC00091344-04, NCGC00091344-05, NCGC00257622-01, AC-12855, AJ-62233, AK106179, AN-24596, CAS-102-07-8, CJ-14055, CJ-14056, KB-79151, SMR000112141, AB1002487, TR-000546, EU-0067898, FT-0606720, ST45141119, L-5305, 4-12-00-00741 (Beilstein Handbook Reference), T6597964, BRD-K13027645-001-02-0, I14-17762, 3B3-033017, N,N inverted exclamation marka-Diphenylurea; Carbanilide, InChI=1/C13H12N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16

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