Sodium Hydroxide → HCID 178465676, compound

HRID 66190

Reaction equation

HRID 66190 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[OH-].[Na+].[CH:8]([S:16](Cl)(=[O:18])=[O:17])=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(C)=O>[CH:8]([S:16]([NH:4][C:2](=[NH:5])[CH3:3])(=[O:18])=[O:17])=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 107500Ethenesulfonyl chloride, 2-phenyl-

Product 1

HCID 178465676HCID 178465676, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of acetamidine hydrochloride (28.8 g., 0.15 mole) and 50% sodium hydroxide (12.0 g., 0.15 mole) in 150 ml. of acetone is stirred for a period of 10 min. to liberate the free base. A solution of styrylsulfonyl chloride (10.1 g., 0.05 mole) in 50 ml. of acetone is added dropwise to the mixture at a temperature of 20°-25° C. with stirring. After further stirring for 10 min., the mixture is concentrated under reduced pressure to remove acetone, the concentrate diluted with 200 ml. of water and acidified with 3N hydrochloric acid to provide a precipitate. The precipitate is collected, dissolved in chloroform and the chloroform extract dried. Evaporation of the chloroform solvent under reduced pressure provides a white solid, m.p. 130°-134° C. which is crystallized from isopropyl acetate affording 8.5 g. (76% yield) of N-(STYRYLSULFONYL)ACETAMIDINE, m.p. 134.5°-137.0° C. (corr.).

Workup

  1. stirringAfter further stirring for 10 min.
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customto remove acetone
  4. additionthe concentrate diluted with 200 ml
  5. customto provide a precipitate
  6. customThe precipitate is collected
  7. dissolutiondissolved in chloroform
  8. extractionthe chloroform extract
  9. customdried
  10. customEvaporation of the chloroform solvent under reduced pressure
  11. customprovides a white solid, m.p. 130°-134° C. which
  12. customis crystallized from isopropyl acetate affording 8.5 g

Sources & evidence

ORD record
ord-aa709b6c2bbc49e9bec13499010138ec
Source dataset
uspto-grants-1978_12
Patent number
US04130663

Linked notes

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