Water → 2-Chloro-N-[2-(2H-[1,2,4]triazol-3-yl)-4-trifluoromethoxy-phenyl]-acetamide

HRID 2066404Notes

Reaction equation

HRID 2066404 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([C:11]2[NH:12][N:13]=[CH:14][N:15]=2)[CH:5]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].O>C(O)(=O)C>[Cl:18][CH2:19][C:20]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:16])[F:17])=[CH:5][C:6]=1[C:11]1[NH:12][N:13]=[CH:14][N:15]=1)=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 686972224-Trifluoromethoxy-2-(2H-[1,2,4]triazol-3-yl)-phenylamine

Product 1

HCID 686936732-Chloro-N-[2-(2H-[1,2,4]triazol-3-yl)-4-trifluoromethoxy-phenyl]-acetamideYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a cooled solution of 4-trifluoromethoxy-2-(2H-[1,2,4]triazol-3-yl)-phenylamine (3.00 g, 12.3 mmol) in acetic acid (62 mL) was added dropwise chloroacetyl chloride (1.96 mL, 24.6 mmol). The resulting light brown suspension was stirred for 20 h at ambient temperature and was then poured into water (246 mL) and stirred for another 3 h. The precipitate was filtered off and washed with water. Drying in vacuo afforded the title compound (3.22 g, 82%) as an off-white solid. MS: m/e=323.1 [M+H]+.

Workup

  1. stirringstirred for another 3 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-aae16ff965634b7ca59c9570113780ab
Source dataset
uspto-grants-2012_10
Patent number
US08293730B2

Reaction notes

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