Ammonia → HCID 18317351, compound

HRID 1700522Notes

Reaction equation

HRID 1700522 reaction equation
[C:1]([C:4]1[C:8]2[C:9](=[O:19])[CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][C:7]=2[O:6][CH:5]=1)(O)=[O:2].CC[N:22]=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.N>ClCCl.O>[C:1]([C:4]1[C:8]2[C:9](=[O:19])[CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][C:7]=2[O:6][CH:5]=1)(=[O:2])[NH2:22]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18317426HCID 18317426, compound

Product 1

HCID 18317351HCID 18317351, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-carboxy-4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran (1.28 g) in dichloromethane (25 ml) were added, under ice-cooling, WSC (1.15 g) and N-hydroxybenzotriazole (0.92 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added concentrated ammonia solution (4.1 g), and the mixture was stirred at room temperature overnight (12 hours). To the reaction solution was added water, and the mixture was subjected to extraction. The lower layer was washed with saturated brine, dried (anhydrous magnesium sulfate) and concentrated under reduced pressure, and the residue was washed with ethyl acetate and isopropylether to give 3-carbamoyl-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.36 g).

Workup

  1. additionwere added, under ice-
  2. temperaturecooling
  3. extractionthe mixture was subjected to extraction
  4. washThe lower layer was washed with saturated brine
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. washthe residue was washed with ethyl acetate and isopropylether

Sources & evidence

ORD record
ord-0c10bc4efb2a40f587f45a88cdebddc8
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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