N-Acetylsulfanilyl chloride → HCID 86734629, compound

HRID 328204Notes

Reaction equation

HRID 328204 reaction equation
[CH2:1]([N:3]1[CH:10]=[C:9]([CH3:11])[C:7]([NH2:8])=[N:6][C:4]1=[O:5])[CH3:2].[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].C(NC1C=CC(S(NC2C(C)=CN(CC)CN=2)(=O)=O)=CC=1)(=O)C>N1C=CC=CC=1>[C:12]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([S:20]([NH:8][C:7]2[C:9]([CH3:11])=[CH:10][N:3]([CH2:1][CH3:2])[C:4](=[O:5])[N:6]=2)(=[O:22])=[O:21])=[CH:18][CH:17]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 8481N-Acetylsulfanilyl chlorideHCID 15218124HCID 15218124, compoundHCID 86734630HCID 86734630, compound

Product 1

HCID 86734629HCID 86734629, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.53 g. of 1-ethyl-5-methylcytosine, 2.34 g. of N-acetylsulfanilyl chloride and 10 ml. of pyridine was stirred overnight, diluted with 100 ml. of cold water, filtered with a little Hyflo to remove turbidity and acidified by addition of 19 ml. of 6N hydrochloric acid. The product was allowed to crystallize for several hours at room temperature before filtering, washing with water, and drying in a vacuum desiccator over potassium hydroxide to obtain 1.78 g. of N4 -acetyl-N1 -(1-ethyl-1,2-dihydro-5-methyl-4-pyrimidinyl)-sulfanilamide, melting at 235°-239°.

Workup

  1. additionA mixture of 1.53 g
  2. additiondiluted with 100 ml
  3. filtrationof cold water, filtered with a little Hyflo
  4. customto remove turbidity
  5. additionacidified by addition of 19 ml
  6. customto crystallize for several hours at room temperature
  7. filtrationbefore filtering
  8. washwashing with water
  9. dry with materialdrying in a vacuum desiccator over potassium hydroxide
  10. customto obtain 1.78 g

Sources & evidence

ORD record
ord-a0952716119046c8a731337e1f0b7350
Source dataset
uspto-grants-1977_04
Patent number
US04016267

Reaction notes

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