Chloroacetyl chloride → Methyl 2-[(chloroacetyl)amino]benzoate

HRID 2175698Notes

Reaction equation

HRID 2175698 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])(O)=O.[Na+].[Cl:17][CH2:18][C:19](Cl)=[O:20]>C1COCC1.O>[Cl:17][CH2:18][C:19]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:20]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8635Methyl AnthranilateHCID 516892Sodium Bicarbonate

Product 1

HCID 295954Methyl 2-[(chloroacetyl)amino]benzoateYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-aminobenzoate (906 mg, 6.0 mmol) and NaHCO3 (554.4 mg, 6.6 mmol) in THF (12 mL) and water (12 mL) at 0° C. was added 2-chloroacetyl chloride (806 mg, 7.2 mmol) dropwise. After 2 hours, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford the crude product. The residue was purified by flash chromatography to give methyl 2-(2-chloroacetamido)benzoate (1.31 g, 96%). LC-MS (ES-API); rt 8.65 min; m/z calculated for C10H10ClNO3 [M+Na]+ 250.0, found 250.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c920318cc0dd485d87b264c5e551b0d8
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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