2,4,6-Trimethylaniline → 1-(3-Nitrophenyl)-3-(mesityl)thiourea

HRID 2235483

Reaction equation

HRID 2235483 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[S:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:13]1([CH3:22])[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:14]=1[NH2:21]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:21][C:14]2[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=2[CH3:22])=[S:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 19050Benzene, 1-isothiocyanato-3-nitro-

Product 1

HCID 204104451-(3-Nitrophenyl)-3-(mesityl)thiourea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.25 g (12.5 mmol) of 3-nitrophenylisothiocyanate and 1.4 mL (10 mmol) of mesityl amine in 10 mL of methanol was stirred at room temperature for 2 h. The resulting precipitate was collected by filtration and dried to give a quantitative yield of 1-(3-nitrophenyl)-3-(mesityl)thiourea. To 1.8 g (5.7 mmol) of the thiourea thus prepared slurried in 20 mL of CCl4 was added 0.35 mL (6.9 mmol) of bromine. The mixture was heated at reflux for 4 h, allowed to cool to room temperature and diluted with dichloromethane. This solution was washed successively with saturated sodium bicarbonate, water and brine before being dried over sodium sulfate. The solution was filtered, concentrated in vacuo and the resulting crude title compound was obtained in quantitative yield and was used without further purification.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-15eb015dcaf2471c83458d0635993b63
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Linked notes

Loading…