Acetone → HCID 178512129, compound

HRID 128405Notes

Reaction equation

HRID 128405 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10]S(C=CC2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[NH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-:27].[Na+].[CH3:29][C:30]([CH3:32])=O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH:29]=[CH:30][C:32]2[CH:25]=[CH:26][C:4]([N+:1]([O-:2])=[O:27])=[CH:5][CH:6]=2)=[NH:9])=[CH:25][CH:26]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 178513470HCID 178513470, compound

Product 1

HCID 178512129HCID 178512129, compoundYield 68%

Procedure

A solution of 4-nitro-N-(4-nitrostyrylsulfonyl)benzamidine (15.0 g., 0.04 mole) and 100 ml. of 2 N sodium hydroxide in 200 ml. of acetone is stirred for 25° C. for a period of 1 hr. Acetone is removed under reduced pressure, the mixture filtered and the filter cake washed with water and dried affording 8.4 g. (68% yield) of 4-nitro-N-(4-nitrostyryl)benzamidine free base, m.p. 214°-216° C. 4-Nitro-N-(4-nitrostyryl)benzamidine hydrochloride obtained in the usual manner has a melting point of 243°-244° C. (dec.). The free base taken up in methanol and acidified with isethionic acid provides 4-NITRO-N-(4-NITROSTYRYL)BENZAMIDINE ISETHIONATE, m.p. 206.5°-208° C., (corr.).

Workup

  1. customAcetone is removed under reduced pressure
  2. filtrationthe mixture filtered
  3. washthe filter cake washed with water
  4. customdried
  5. customaffording 8.4 g

Sources & evidence

ORD record
ord-72350a8b4a2043bc9c836d090a91194e
Source dataset
uspto-grants-1981_03
Patent number
US04259482

Reaction notes

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