Ammonia → 1-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

HRID 1803107Notes

Reaction equation

HRID 1803107 reaction equation
[NH3:1].[F:2][C:3]1[C:4]([N:17]=[C:18]=[S:19])=[CH:5][C:6]([O:15][CH3:16])=[C:7]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)[CH:8]=1>>[F:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)[C:6]([O:15][CH3:16])=[CH:5][C:4]=1[NH:17][C:18]([NH2:1])=[S:19]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 866498891-(5-fluoro-4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole

Product 1

HCID 866498901-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thioureaYield 100.5%

Procedure

Step B (4): Methanolic ammonia (1.0 M, 25 mL, 25 mmol) was added to a flask charged with 1-(5-fluoro-4-isothiocyanato-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole (870 mg, 3.29 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 in vacuo. The resulting solid was dried under high vacuum to afford 1-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (930 mg, 100% yield). LC-MS (M+H)+ 282.1. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.84 (s, 1 H) 7.88 (d, J=6.41 Hz, 1 H) 7.57 (d, J=10.99 Hz, 1 H) 3.86 (s, 3 H) 2.36 (s, 3 H).

Workup

  1. additionAfter the addition
  2. waitAfter 24 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe resulting solid was dried under high vacuum

Sources & evidence

ORD record
ord-722d3f53831c4ef1a257f73067a10e87
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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