N-Acetylsulfanilyl chloride → HCID 86734626, compound

HRID 328202Notes

Reaction equation

HRID 328202 reaction equation
[CH:1]1([N:4]2[CH:11]=[CH:10][C:8]([NH2:9])=[N:7][C:5]2=[O:6])[CH2:3][CH2:2]1.[C:12]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([S:20](Cl)(=[O:22])=[O:21])=[CH:18][CH:17]=1)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([S:20]([NH:9][C:8]2[CH:10]=[CH:11][N:4]([CH:1]3[CH2:3][CH2:2]3)[C:5](=[O:6])[N:7]=2)(=[O:22])=[O:21])=[CH:18][CH:17]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 21444304HCID 21444304, compound

Product 1

HCID 86734626HCID 86734626, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 10.6 g. of 1-cyclopropylcytosine, 16.4 g. of N-acetylsulfanilyl chloride and 47 ml. of pyridine was stirred overnight after momentary cooling to maintain the reaction below 30°. The mixture was poured into 700 ml. of water, and after filtration by gravity, the solution was strongly acidified by addition of 6N hydrochloric acid. Gradual crystallization occurred overnight in a refrigerator before filtering the N4 -acetyl-N1 -(1-cyclopropyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-sulfanilamide; yield 10.7 g., m.p. 139°-143°.

Workup

  1. additionA mixture of 10.6 g
  2. temperatureafter momentary cooling
  3. temperatureto maintain
  4. customthe reaction below 30°
  5. additionThe mixture was poured into 700 ml
  6. filtrationof water, and after filtration by gravity
  7. additionthe solution was strongly acidified by addition of 6N hydrochloric acid
  8. customGradual crystallization
  9. filtrationbefore filtering the N4 -acetyl-N1 -(1-cyclopropyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-sulfanilamide

Sources & evidence

ORD record
ord-fee3259df9034774a0248d88d966ef8a
Source dataset
uspto-grants-1977_04
Patent number
US04016267

Reaction notes

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