Ammonia → 1-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

HRID 1803126Notes

Reaction equation

HRID 1803126 reaction equation
[NH3:1].[N:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[N:14][C:13]([CH3:16])=[N:12]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[N:11]1[CH:15]=[N:14][C:13]([CH3:16])=[N:12]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 866498971-(4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole

Product 1

HCID 866498981-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thioureaYield 87%

Procedure

Step F (4): Methanolic ammonia (1.0 M, 100 mL, 100 mmol) was added to a flask charged with 1-(4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole (3.91 g, 15.88 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 to afford 1-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (4.18 g, 13.81 mmol, 87% yield) as a white solid. LC-MS (M+H)+ 264.0.

Workup

  1. additionAfter the addition
  2. waitAfter 24 h
  3. concentrationthe reaction mixture was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-dcfec4c45e0947f4899640acac3ce3a2
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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