Sodium Hydroxide → HCID 178465676, compound

HRID 839551Notes

Reaction equation

HRID 839551 reaction equation
[N+]([C:4]1[CH:24]=[CH:23][C:7]([CH:8]=[CH:9][S:10]([NH:13][C:14](=[NH:22])[C:15]2C=CC(N)=CC=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.Cl.C(N)(=N)C.[OH-].[Na+].C(S(Cl)(=O)=O)=CC1C=CC=CC=1>CC(C)=O>[CH:9]([S:10]([NH:13][C:14](=[NH:22])[CH3:15])(=[O:12])=[O:11])=[CH:8][C:7]1[CH:23]=[CH:24][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 107500Ethenesulfonyl chloride, 2-phenyl-HCID 178513469HCID 178513469, compound

Product 1

HCID 178465676HCID 178465676, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Addition of 50% sodium hydroxide (4.0 g., 0.05 mole) to a solution of 4-aminobenzamidine hydrochloride (0.5 mole) in 10 ml. of water affords 4-aminobenzamidine free base. Acetone (50 ml.) is added to the liberated free base and the mixture cooled to 5° C. 4-Nitrostyrylsulfonyl chloride is added to the mixture in a period of 5 min. while maintaining a temperature below 15° C. The mixture is stirred for 10 min., the reaction mixture concentrated under reduced pressure provides a residue which diluted with 100 ml. of water and neutralized with 3N hyrochloric acid affords a pale yellow solid precipitate. The precipitate is collected, washed thoroughly with water and then triturated first with isopropanol and then with ether to yield 7.3 g. (84%) of N-(4-NITROSTYRYLSULFONYL)-4-AMINOBENZAMIDINE, m.p. 188°-189° C. (b) 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. customThe precipitate is collected
  2. washwashed thoroughly with water
  3. customtriturated first with isopropanol
  4. customwith ether to yield 7.3 g
  5. stirringAfter further stirring for 10 min.
  6. concentrationthe mixture is concentrated under reduced pressure
  7. customto remove acetone
  8. additionthe concentrate diluted with 200 ml
  9. customto provide a precipitate
  10. customThe precipitate is collected
  11. dissolutiondissolved in chloroform
  12. extractionthe chloroform extract
  13. customdried
  14. customEvaporation of the chloroform solvent under reduced pressure
  15. customprovides a white solid, m.p. 130°-134° C. which
  16. customis crystallized from isopropyl acetate affording 8.5 g

Sources & evidence

ORD record
ord-e1ac307a80064a9fa2f51393a3fd941c
Source dataset
uspto-grants-1978_06
Patent number
US04096183

Reaction notes

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