Triethylamine → Methyl 2-[[2-(1-methylethoxy)acetyl]amino]benzoate

HRID 1534854Notes

Reaction equation

HRID 1534854 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(N(CC)CC)C.[CH:19]([O:22][CH2:23][C:24](Cl)=[O:25])([CH3:21])[CH3:20]>ClCCl>[CH:19]([O:22][CH2:23][C:24]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])=[O:25])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 12266979Acetyl chloride, (1-methylethoxy)-

Product 1

HCID 15084049Methyl 2-[[2-(1-methylethoxy)acetyl]amino]benzoateYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.90 g (33 mmol) of methyl anthranilate and 6.1 ml of triethylamine in 50 ml of dichloromethane was dropwise added a solution of 4.43 g (33 mmol) of isopropoxyacetylchloride in 20 ml of dichloromethane under chilling with ice for a period of 15 min. The resulting mixture was stirred over night at room temperature. The reaction mixture was washed sequentially with 5 % aqueous sodium carbonate, 3 N hydrochloric acid and 5% aqueous sodium carbonate, and then was dried over anhydrous sodium sulfate. The solvent was distilled off to leave 5.59 g of the desired compound as a residual pale brown oil. (Yield: 68.6 %)

Workup

  1. temperatureunder chilling with ice for a period of 15 min
  2. washThe reaction mixture was washed sequentially with 5 % aqueous sodium carbonate, 3 N hydrochloric acid and 5% aqueous sodium carbonate
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-05c83e4cf4f3418f9649c982cc91d98d
Source dataset
uspto-grants-1992_02
Patent number
US05091403

Reaction notes

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