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

HRID 1803112Notes

Reaction equation

HRID 1803112 reaction equation
[NH3:1].[F:2][C:3]1[CH:8]=[C:7]([N:9]=[C:10]=[S:11])[CH:6]=[CH:5][C:4]=1[N:12]1[C:16]([CH3:17])=[N:15][CH:14]=[N:13]1>>[F:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]([NH2:1])=[S:11])[CH:6]=[CH:5][C:4]=1[N:12]1[C:16]([CH3:17])=[N:15][CH:14]=[N:13]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 866498911-(2-fluoro-4-isothiocyanatophenyl)-5-methyl-1H-1,2,4-triazole

Product 1

HCID 866498921-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)thioureaYield 94%

Procedure

Step C (4): Methanolic ammonia (1.0 M, 100 mL, 100 mmol) was added to a flask charged with 1-(2-fluoro-4-isothiocyanatophenyl)-5-methyl-1H-1,2,4-triazole (3.18 g, 13.6 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-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (3.21 g, 94% yield) as an off-white solid. LC-MS (M+H)+ 252.1. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.06 (s, 1 H), 7.93 (dd, J=12.8, 2.1 Hz, 1 H), 7.54 (t, J=8.7 Hz, 1 H), 7.37 (dd, J=8.5, 1.8 Hz, 1 H), 2.32 (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-8569c34745b943b18a3c9c72d7b8613d
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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