Ammonia → 1-(3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)thiourea

HRID 1803145Notes

Reaction equation

HRID 1803145 reaction equation
[NH3:1].[N:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=2)=[C:7]([O:17][CH3:18])[CH:6]=1)=[C:3]=[S:4]>>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([NH:2][C:3]([NH2:1])=[S:4])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 866499074-(4-isothiocyanato-2-methoxyphenyl)-1-methyl-1H-pyrazole

Product 1

HCID 866499081-(3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)thioureaYield 86.5%

Procedure

Step K (4): Methanolic ammonia (2.0 M, 20 mL, 40 mmol) was added to a flask charged with 4-(4-isothiocyanato-2-methoxyphenyl)-1-methyl-1H-pyrazole (1.46 g, 5.95 mmol). After 3 h, the reaction mixture was concentrated in vacuo. The solid was triturated with diethyl ether. The solid was collected by vacuum filtration and dried under high vacuum to afford 1-(3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)thiourea (1.35 g, 86% yield). LC-MS (M+H)+ 263.1.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe solid was triturated with diethyl ether
  3. filtrationThe solid was collected by vacuum filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-1867edefc8ae481fa0338eba781a3c70
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…