Triethylamine → HCID 19792116, compound

HRID 1655464Notes

Reaction equation

HRID 1655464 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:20](Cl)(=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[Cl:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:20](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoate

Product 1

HCID 19792116HCID 19792116, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-amino-5-chlorobenzoate (15 g) and triethylamine (12 ml) in methylene chloride (150 ml) was added dropwise, while stirring under ice-cooling, valeryl chloride (10 ml). The mixture was stirred at room temperature for further two hours. The reaction mixture was washed with an aqueous solution of sodium bicarbonate and water, followed by drying. The solvent was distilled off to afford a pale yellow crystals (13.4 g, 61%), m.p. 48-49° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for further two hours
  3. washThe reaction mixture was washed with an aqueous solution of sodium bicarbonate and water
  4. customby drying
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-04ad8f63b43543d79bcc5df67637cbab
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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