Benzoyl isothiocyanate → 1-Benzoyl-3-(2,6-dibromo-4-fluoro-phenyl)-thiourea

HRID 408753Notes

Reaction equation

HRID 408753 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[NH2:10].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:11]([NH:19][C:20]([NH:10][C:3]1[C:2]([Br:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[Br:9])=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 2428722,6-Dibromo-4-fluoroaniline

Product 1

HCID 866512491-Benzoyl-3-(2,6-dibromo-4-fluoro-phenyl)-thioureaYield 85.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 2,6-dibromo-4-fluoro-phenylamine (1.00 g, 3.72 mmol), benzoyl isothiocyanate (0.600 ml, 4.46 mmol), dimethyl-pyridin-4-yl-amine (45.0 g, 0.370 mmol), and toluene (5 ml) was stirred at 23° C. for 16 hours. The resulting precipitate was collected by filtration and washed with hexane to yield titled compound (1.37 g, 85%). MS (ESI/CI): mass calcd. for C14H9Br2FN2OS, 429.9; m/z found, 430.9 [M+H]+. 1H NMR (400 MHz, CD3OD-d4): 8.05-7.98 (m, 2H), 7.73-7.66 (m, 1H), 7.62-7.55 (m, 4H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with hexane

Sources & evidence

ORD record
ord-934274ab6c6846e187c29af9b99487ad
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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