Triethylamine → Phenylcarbamoylmethyl acetoacetate

HRID 890143Notes

Reaction equation

HRID 890143 reaction equation
[OH:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].C(N(CC)CC)C.[CH2:19]=[C:20]1[O:24][C:22](=[O:23])[CH2:21]1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:22]([O:1][CH2:2][C:3](=[O:4])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:23])[CH2:21][C:20]([CH3:19])=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12661DiketeneHCID 2642602-Hydroxy-N-phenylacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 22250379Phenylcarbamoylmethyl acetoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.36 g (28.8 mmol)) of 2-hydroxy-N-phenylacetamide, 0.8 ml (5.74 mmol) of triethylamine and 6.5 ml (84.3 mmol) of diketene were heated at 70° C. under stirring in 50 ml of toluene for 7.5 hours. After the addition of a saturated aqueous sodium hydrogencarbonate solution at room temperature followed by the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. extractionfollowed by the extraction with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adf6b218092747a799c2e77d9687103d
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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