Pyridine → 5-Chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl ester

HRID 1095011Notes

Reaction equation

HRID 1095011 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].N1C=CC=CC=1.[Cl:19][CH2:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][CH:29]=[C:21]([CH2:20][Cl:19])[CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 231072215-Chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-chloro-benzoic acid methyl ester (1.5 g) was dissolved in anhydrous methylene chloride (25 ml). Pyridine (1.4 ml) and 3-(chloromethyl)benzoyl chloride (1.4 ml) were added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was then washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to precipitate crystals. The precipitated crystals were collected by filtration through Kiriyama Rohto and were washed with ether to give 5-chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl ester as a useful intermediate (2.4 g, yield 90%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was then washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customto precipitate crystals
  9. filtrationThe precipitated crystals were collected by filtration through Kiriyama Rohto
  10. washwere washed with ether

Sources & evidence

ORD record
ord-d0729293249b40d0b6cf90ad073a461c
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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