Triethylamine → HCID 1731778, compound

HRID 1534856Notes

Reaction equation

HRID 1534856 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.[CH2:19]([O:21][CH2:22][C:23](Cl)=[O:24])[CH3:20]>ClCCl>[CH2:19]([O:21][CH2:22][C:23]([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:24])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 84189Ethoxyacetyl chloride

Product 1

HCID 1731778HCID 1731778, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.53 g (30 mmol) of methyl anthranilate and 6.1 ml of triethylamine in 50 ml of dichloromethane was dropwise added a solution of 4.41 g (36 mmol) of ethoxyacetylchloride in 10 ml of dichloromethane under chilling with ice for a period of 15 min. The resulting mixture was stirred for 1 hr. at room temperature. The stirred mixture was washed sequentially with water, 4 N hydrochloric acid and 5% aqueous sodium carbonate, and then was dried over anhydrous sodium sulfate. The solvent was distilled off to leave 7.66 g of the desired compound (purity: 92.8 %) as a residual pale brown oil.

Workup

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

Sources & evidence

ORD record
ord-b8a6f5e70b8e4eb1a76c90e9986ad0e1
Source dataset
uspto-grants-1992_02
Patent number
US05091403

Reaction notes

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