Acetone → N-phenylmorpholine-4-carboxamide

HRID 1903286Notes

Reaction equation

HRID 1903286 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CC(C)=O.[SH2]=N.[C:13]1([NH:19][C:20](C2C=CC=CC=2C(O)=O)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[C:13]1([NH:19][C:20]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 8083MorpholineHCID 178514671HCID 178514671, compound

Product 1

HCID 341876N-phenylmorpholine-4-carboxamideYield 32.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.9 g morpholine with 5 ml aceton was added dropwise during 5 minutes to a suspension of 1.5 g phenylcarbamoyl-benzoic acid sulfimide with 20 ml acetone, under stirring. The reaction mixture was stirred for a further 30 minutes at ambient temperature, then diluted with 150 ml water. Acetone was distilled off, the mixture was cooled, and 0.35 g phenylcarbamoyl-morpholine was isolated by filtration. The white crystalline material melted at 160°-162° C.

Workup

  1. stirringThe reaction mixture was stirred for a further 30 minutes at ambient temperature
  2. distillationAcetone was distilled off
  3. temperaturethe mixture was cooled

Sources & evidence

ORD record
ord-5bb3a2076b7546c3b513ae404a534555
Source dataset
uspto-grants-1984_03
Patent number
US04435567

Reaction notes

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