Diethylamine → HCID 19699005, compound

HRID 1490349Notes

Reaction equation

HRID 1490349 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O)(=[O:10])[CH2:8][CH3:9].[CH2:21]([N:23](CC)[CH2:24][CH3:25])[CH3:22].C(NCC)C>C(Cl)Cl.C(OCC)(=O)C.CN(C)C=O>[C:7]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([N:23]([CH2:24][CH3:25])[CH2:21][CH3:22])=[O:16])(=[O:10])[CH2:8][CH3:9]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 959382-Propionyloxybenzoic acid

Product 1

HCID 19699005HCID 19699005, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

2.0 ml (23 mmole) of oxalyl chloride and 0.050 ml of N,N-dimethylformamide were added, whilst ice-cooling, to a solution of 2.40 g (12.4 mmole) of 2-propionyloxybenzoic acid in 24 ml of methylene chloride, and the resulting mixture was stirred for 1 hour. At the end of this time, the solvent and excess oxalyl chloride were removed by distillation under reduced pressure, and 20 ml of methylene chloride were added to the residue. 1.36 g (13.5 mole) of triethylamine and 986 mg (13.5 mmole) of diethylamine were then added, whilst ice-cooling, to the resulting solution, and the mixture was stirred for 1 hour. The mixture was then diluted with ethyl acetate, and the organic layer was washed with water. The solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through 25 g of silica gel, using a gradient elution method, with mixtures of methylene chloride and ethyl acetate ranging from 10:1 to 7:1 by volume as the eluent, to give 3.0 g (yield 97%) of 2-diethylaminocarbonylphenyl propionate as an oil.

Workup

  1. customAt the end of this time, the solvent and excess oxalyl chloride were removed by distillation under reduced pressure, and 20 ml of methylene chloride
  2. additionwere added to the residue
  3. temperaturecooling, to the resulting solution
  4. stirringthe mixture was stirred for 1 hour
  5. washthe organic layer was washed with water
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue was purified by column chromatography through 25 g of silica gel
  8. washa gradient elution method

Sources & evidence

ORD record
ord-93d31fa0ba4d4cd6a57818dad74b4f3b
Source dataset
uspto-grants-1997_10
Patent number
US05681951

Reaction notes

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