Synthesis of phenothiazine

Preparation of phenothiazine

Preparation of phenothiazine

Preparation of phenothiazine

22 g of diphenylamine, 8.2 g of sulfur, and 3.2 gms. of anhydrous aluminum chloride are melted together. The reaction sets 140-150° C with the rapid evolution of hydrogen sulfide; by lowerg the temperature, a few degrees the reaction can be slackened. Wen the reaction has moderated, the temperature is raised to 160° C for a time. The melt, when cool, is ground up and extracted, first with water and then with dilute alcohol. The residue consists of almost pure phenothiazine. It can be recrystallised from alcohol. Yield 93%, yellowish leaflets; m.p. 180° C.

Systematic organic chemistry, by W. M. Cumming, 325-326, 1937.

IUPAC Name

10H-phenothiazine

InChI

InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H

InChI Key

WJFKNYWRSNBZNX-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)NC3=CC=CC=C3S2

MeSH Synonyms

phenosan, phenothiazine

Depositor-Supplied Synonyms

PHENOTHIAZINE, 10H-Phenothiazine, 92-84-2, Thiodiphenylamine, Feeno, Dibenzothiazine, Phenthiazine, Phenosan, Dibenzo-1,4-thiazine, Agrazine, Antiverm, Contaverm, Fenoverm, Fentiazin, Helmetina, Lethelmin, Nemazene, Nemazine, Nexarbol, Padophene, Penthazine, Phenegic, Phenoverm, Phenovis, Phenoxur, Phenzeen, Souframine, Orimon, Reconox, Thiodiphenylamin, Wurm-Thional, Early bird wormer, AFI-Tiazin, Dibenzoparathiazine, Dibenzo-p-thiazine, Fenothiazine, Fenotiazina, Tiodifenilamina, Biverm, Thiodifenylamine, 10H-Phenothiazin, Phenthiazinum, ENT 38, XL-50, Fenothiazine [Dutch], Caswell No. 652, Fenotiazina [Italian], Thiodifenylamine [Dutch], Thiodiphenylamin [German], Tiodifenilamina [Italian], UNII-GS9EX7QNU6, CHEMBL828, EPA Pesticide Chemical Code 064501, Fenotiazina [INN-Spanish], Phenothiazinum [INN-Latin], C12H9NS, CCRIS 5877, CHEBI:37931, HSDB 5279, WJFKNYWRSNBZNX-UHFFFAOYSA-N, NSC 2037, EINECS 202-196-5, Phenothiazine (INN), Phenothiazine [INN], BRN 0143237, NCGC00091146-02, NCGC00091146-04, AI3-00038, DSSTox_CID_1126, DSSTox_RID_75957, DSSTox_GSID_21126, CAS-92-84-2, SMR000059045, phenothiazin, Danikoropa, Phenothiazinum, ZINC00028150, ACMC-209rhv, Phenothiazine [INN:NF], 10h-phenothiazin-10-yl, GS9EX7QNU6, PS733_SUPELCO, AC1L1O0Y, AC1Q1HN9, cid_7108, SCHEMBL9114, Nemazine [veterinary] (TN), Oprea1_495637, P14831_ALDRICH, KSC223I7B, MLS000069413, MLS001424182, MLS002152928, MLS003166904, BIDD:GT0831, 46624_RIEDEL, SCHEMBL2395921, 10H-PHENOTHIAZIN-1-YL, 46624_FLUKA, WLN: T C666 BM ISJ, NSC2037, MolPort-001-779-815, BB_SC-7173, HMS1607G06, HMS2052I13, HMS2230N12, HMS3372C18, HMS3394I13, Pharmakon1600-01506171, 10H-Dibenzo[b,e][1,4]thiazine, 2,3:5,6-Dibenzo-1,4-thiazine, NSC-2037, 10H-dibenzo-[b,e]-1,4-thiazine, Tox21_111090, Tox21_400010, ANW-39905, AR-1J0739, BBL011728, BDBM50012855, NSC760392, SBB056680, STK205834, AKOS000119180, Tox21_111090_1, ZINC100009616, CCG-101115, LS-1938, MCULE-2058587296, NC00365, NE10371, NSC-760392, PS-3980, RL05846, RTR-031091, TRA0027963, NCGC00091146-01, NCGC00091146-03, NCGC00091146-05, NCGC00091146-08, AC-10429, AJ-08470, AK106259, AN-24244, CPD000059045, DR000309, K692, PL014732, PL046330, PL075520, SAM001246855, SC-25961, ST001368, ZB000821, AB1006775, KB-217605, TR-031091, FT-0654203, P0106, ST24038227, D02601, J10398, 4-27-00-01214 (Beilstein Handbook Reference), SR-01000721844, 3B2-1606, I09-0332, SR-01000721844-3, SR-01000721844-4, T7105874, W-100270, I14-23303, S4251,92-84-2, 8023-30-1, InChI=1/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13

Removed Synonyms

Vermitin, null, CID7108, C031637, 76674-21-0, 8048-22-4, 98736-47-1, PTZ

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