Pyridine → 2-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide

HRID 1453792Notes

Reaction equation

HRID 1453792 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15].N1C=CC=CC=1>ClCCl>[Cl:1][CH2:2][C:3]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([Cl:6])=[C:8]([C:14]([F:17])([F:15])[F:16])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 23077292-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Chloroacetic acid chloride (0.69 ml; 8.44 mmol) is dropped slowly into a stirred solution of 4-chloro-3-trifluoro methyl aniline (1.5 g; 7.67 mmol) in pyridine (0.81 ml; 9.97 mmol) and dichloromethane (15 ml), cooled to 0° C. Stirring is continued for 2 h at room temperature. The reaction mixture is diluted with dichloromethane, washed twice with 1N aqueous hydrochloric acid and with water. The reaction mixture is then dried over Na2SO4, filtered and evaporated to yield 2.05 g (98%) brownish solid of 9.

Workup

  1. washwashed twice with 1N aqueous hydrochloric acid and with water
  2. dry with materialThe reaction mixture is then dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-30d3de86a9bc433d926c7be42cf49a6c
Source dataset
uspto-grants-2009_01
Patent number
US07476683B2

Reaction notes

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