Dimethylformamide → 4-chloro-N,N-diethyl-2-(trifluoromethyl)benzamide

HRID 2100606Notes

Reaction equation

HRID 2100606 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])=[O:8])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 65578Oxalyl chlorideHCID 27738564-Chloro-2-(trifluoromethyl)benzoic acid

Product 1

HCID 690558204-chloro-N,N-diethyl-2-(trifluoromethyl)benzamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4-chloro-2-(trifluoromethyl)benzoic acid (18.1 g, 80 mmol) in 500 mL of methylene chloride was added oxalyl chloride (60 mL of a 2.0 M solution in methylene chloride, 120 mmol) followed by N,N-dimethylformamide (0.2 mL). The reaction was allowed to stir at ambient temperature for 18 h. The volatiles were removed in vacuo to afford the crude acid chloride intermediate. The residue was taken up in 500 mL of methylene chloride and then there was added diethylamine (16.5 mL, 160 mmol). The resulting solution was allowed to stir at ambient temperature for 2 h, and then the mixture was concentrated to an oil. The residue was purified (ISCO, 0-30% EtOAc/hexane, 45 min) to afford 11.4 g (51%) of the title compound as a pale yellow oil.

Workup

  1. customThe volatiles were removed in vacuo
  2. customto afford the crude acid chloride intermediate
  3. stirringto stir at ambient temperature for 2 h
  4. concentrationthe mixture was concentrated to an oil
  5. customThe residue was purified (ISCO, 0-30% EtOAc/hexane, 45 min)

Sources & evidence

ORD record
ord-db3fbee541414173a688f18645dbddf3
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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