Dimethylsulphamoyl chloride → HCID 54319481, compound

HRID 1287846Notes

Reaction equation

HRID 1287846 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]([NH2:30])[CH:17]=1)=[O:15]>N1C=CC=CC=1.O>[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:18]([NH:30][S:3](=[O:5])(=[O:4])[N:2]([CH3:7])[CH3:1])[CH:17]=1)=[O:15]

Participants

5

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 53880974[3-Amino-4-(benzyloxy)phenyl](pyridin-2-yl)methanone

Product 1

HCID 54319481HCID 54319481, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent2×

Procedure

A solution of 4.7 g (32.8 mmol) of dimethylsulfamyl chloride in 5 ml of dry pyridine is added to 5.0 g (16.4 mmol) of 3-amino-4-benzyloxyphenyl 2-pyridyl ketone in 100 ml of dry pyridine at 0°-10° C. The reaction mixture is stirred in the cold overnight and then poured in water and extracted with ether. The ether extract is washed with water and extracted with dilute aqueous KOH. This basic extract is washed with ether, acidified with hydrochloric acid and extracted with methylene chloride. The dried organic extract is evaporated in vacuo to give 4-benzyloxy-3-dimethylsulfamoylaminophenyl 2-pyridyl ketone. Hydrogenation over PcO2 according to the procedure of Example 3 gives α-(4-hydroxy-3-dimethylsulfamoylaminophenyl)-2-piperidylcarbinol.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. extractionextracted with dilute aqueous KOH
  5. extractionThis basic extract
  6. washis washed with ether
  7. extractionextracted with methylene chloride
  8. extractionThe dried organic extract
  9. customis evaporated in vacuo

Sources & evidence

ORD record
ord-0fd166a0ff4f4d43964d065de08ba4fc
Source dataset
uspto-grants-1976_10
Patent number
US03985887

Reaction notes

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