1-Bromo-2-isothiocyanatobenzene → N-(4-cyano-2-hydroxyphenyl)-N'-(2-bromophenyl) thiourea

HRID 413341Notes

Reaction equation

HRID 413341 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([OH:10])[CH:4]=1)#[N:2].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]=[S:20]>C(O)C>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Br:11])=[S:20])=[C:5]([OH:10])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 6116541-Bromo-2-isothiocyanatobenzeneHCID 101977194-Amino-3-hydroxybenzonitrile

Product 1

HCID 12043084N-(4-cyano-2-hydroxyphenyl)-N'-(2-bromophenyl) thioureaYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-cyano-2-hydroxyl aniline (1.0 g, 7.5 mmol) in ethanol (20 mL) was added 2-bromophenylisothiocyanate (1.0 mL, 7.5 mmol). After 24 h, the reaction mixture was concentrated under reduced pressure to give 2.0 g (77%) of N-(4-cyano-2-hydroxyphenyl)-N′-(2-bromophenyl) thiourea as a yellow solid which required no further purification. 1H NMR (400 MHz, DMSO) δ 10.8 (s, 1H), 10.1 (s, 1H), 9.6 (s, 1H), 8.7 (d, 1H), 7.7 (d, 1H), 7.6 (d, 1H), 7.4 (t, 1H), 7.25 (d, 1H and d, 2H); MS(EI) m/e 229 (100), 348 (75 (M+)), 462 (30), 695 (10).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-653e2694b6724ce6893f380c7c9f4c12
Source dataset
uspto-grants-2003_05
Patent number
US06566387B1

Reaction notes

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