Synthesis of dibenzyl sulfide

Preparation of dibenzyl sulfide

Preparation of dibenzyl sulfide

Preparation of dibenzyl sulfide

1.5 mole of sodium sulfide nonahydrate is dissolved in 250 ml of water and 50 ml of methanol in a three-necked flask fitted with a reflux condenser, dropping funnel, and stirrer. Then 2 moles of the appropriate benzyl bromide is added and the mixture is boiled under reflux with very vigorous stirring for 5 hours. After cooling, the reaction mixture is extracted with ether, the ethereal layer is separated off, the aqueous solution is additionally extracted several times with ether several times, and the combined organic phases are washed with 10% caustic sodium carbonate and finally with water. The ether is distilled and obtained solid is washed with water, and crystallized from methanol yielding 85%, m.p. 49 °C °C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 215-216, (1973)

IUPAC Name

benzylsulfanylmethylbenzene

InChI

InChI=1S/C14H14S/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2

InChI Key

LUFPJJNWMYZRQE-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)CSCC2=CC=CC=C2

MeSH Synonyms

benzyl sulfide, dibenzyl sulfide

Depositor-Supplied Synonyms

Dibenzyl sulfide, BENZYL SULFIDE, 538-74-9, Dibenzyl sulphide, Benzyl thioether, Benzyl monosulfide, Dibenzyl monosulfide, Dibenzyl thioether, Benzene, 1,1′-[thiobis(methylene)]bis-, 1,3-Diphenyl-2-thiapropane, benzylsulfanylmethylbenzene, Sulfide, dibenzyl, [(Benzylsulfanyl)methyl]benzene, 1,1′-(Thiobis(methylene))bisbenzene, NSC 212544, CCRIS 5969, HSDB 2794, LUFPJJNWMYZRQE-UHFFFAOYSA-N, EINECS 208-703-6, 1,1′-[thiobis(methylene)]dibenzene, SBB058652, Benzene, 1,1′-(thiobis(methylene))bis-, AI3-00842, phenyl(phenylmethylthio)methane, Benzene,1′-[thiobis(methylene)]bis-, dibenzylsulfane, Dibenzylsulphide, Sulfide, dibenzyl-, DIBENZYL-SULFIDE, SULFIDE,DIBENZYL, PubChem10847, ACMC-209lap, Benzyl sulfide (8CI), DSSTox_CID_4599, SCHEMBL206, ((Benzylthio)methyl)benzene, AC1L1W4B, DSSTox_RID_77463, DSSTox_GSID_24599, MLS002152894, (phenylmethylthio)methylbenzene, 33820_ALDRICH, CHEMBL1369381, SCHEMBL11075647, 33820_FLUKA, CTK3J0485, NSC6648, (phenylmethylsulfanyl)methylbenzene, MolPort-001-782-732, HMS2270O24, UNII-Q08048624M, NSC-6648, ZINC1874356, Tox21_200326, ANW-31871, NSC212544, STL482503, ZINC01874356, AKOS003626437, LS-1334, MCULE-2863865808, NSC-212544, RP26839, RTR-019039, TRA0040611, 1,1′-(sulfanediyldimethanediyl)dibenzene, Benzene,1,1′-[thiobis(methylene)]bis-, NCGC00091191-01, NCGC00091191-02, NCGC00257880-01, AC-16469, AN-45716, CAS-538-74-9, CJ-30710, KB-76496, OR020097, OR280864, SC-46252, SMR000112558, DB-052416, TR-019039, B0440, FT-0624646, Q08048624M, ST50405871, A829811, I01-2095, 3B3-026363, InChI=1/C14H14S/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H

Removed Synonyms

CID10867, c0897

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