Triethylamine → 4-chloro-2-fluoro-N-methoxy-N-methylbenzamide

HRID 1744874Notes

Reaction equation

HRID 1744874 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:11])[CH:3]=1.Cl.[CH3:13][NH:14][O:15][CH3:16].CCN=C=NCCCN(C)C.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([O:15][CH3:16])[CH3:13])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 991524-Chloro-2-fluorobenzoic acid

Product 1

HCID 222258304-chloro-2-fluoro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 4-chloro-2-fluorobenzoic acid (1 eq) in CH2Cl2 (1.6 M) was added N,O-dimethylhydroxylamine hydrochloride (1.5 eq), EDCI (1.5 eq) and triethylamine (4 eq). The reaction mixture was stirred at rt for 16 hrs, concentrated and 0.5M aqueous citric acid was added. The mixture was extracted with 1:1 EtOAc:Et2O. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give 4-chloro-2-fluoro-N-methoxy-N-methylbenzamide, which was used as such for the next step.

Workup

  1. concentrationconcentrated
  2. addition0.5M aqueous citric acid was added
  3. extractionThe mixture was extracted with 1:1 EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d9b38f79a6b434ea99d12e7ca6d779c
Source dataset
uspto-grants-2006_03
Patent number
US07019022B2

Reaction notes

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