Ammonia → 1-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thiourea

HRID 1803102Notes

Reaction equation

HRID 1803102 reaction equation
[NH3:1].[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[S:16])=[CH:10][C:9]=2[O:17][CH3:18])[CH:7]=1>>[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:1])=[S:16])=[CH:10][C:9]=2[O:17][CH3:18])[CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 866498874-chloro-1-(4-isothiocyanato-2-methoxy-phenyl)-1H-imidazole

Product 1

HCID 866498881-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thioureaYield 84.6%

Procedure

Step A (4): Methanolic ammonia (1.0 M, 100 mL, 100 mmol) was added to a flask charged with 4-chloro-1-(4-isothiocyanato-2-methoxy-phenyl)-1H-imidazole (4.27 g, 16.1 mmol) in a ice-water bath. After the addition was complete, the resulting slurry was stirred for 10 min and then allowed to warm to rt. After 24 h, the reaction mixture was concentrated to dryness in vacuo. The solid was suspended in ethanol (200 mL) and stirred for 2 hours. The solid was collected by vacuum filtration and dried under high vacuum for 24 h to afford 1-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thiourea (3.85 g, 83% yield) as a white solid. LC-MS (M+H)+ 283.0.

Workup

  1. additionAfter the addition
  2. waitAfter 24 h
  3. concentrationthe reaction mixture was concentrated to dryness in vacuo
  4. stirringstirred for 2 hours
  5. filtrationThe solid was collected by vacuum filtration
  6. customdried under high vacuum for 24 h

Sources & evidence

ORD record
ord-6c23389b468c4d8aa17b66878dd4a8da
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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