Hydrochloric Acid → HCID 178479333, compound

HRID 839547Notes

Reaction equation

HRID 839547 reaction equation
NC1C=CC(C(NS(C=CC2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=N)=CC=1.[OH-].[Na+].[N+:27]([C:30]1[CH:47]=[CH:46][C:33]([CH:34]=[CH:35][NH:36][C:37](=[NH:45])[C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)=[CH:32][CH:31]=1)([O-:29])=[O:28].[ClH:48]>O.CC(C)=O>[ClH:48].[NH2:44][C:41]1[CH:40]=[CH:39][C:38]([C:37]([NH:36][CH:35]=[CH:34][C:33]2[CH:46]=[CH:47][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=2)=[NH:45])=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178512128HCID 178512128, compoundHCID 178513469HCID 178513469, compound

Product 1

HCID 178479333HCID 178479333, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 4-amino-N-(4-nitrostyrylsulfonyl)benzamidine (6.9 g., 0.02 mole) in 120 ml. of acetone is stirred with 50% sodium hydroxide (6.4 g., 0.08 mole) in 40 ml. of water for 1 hr. Concentration of the reaction mixture affords a residue which is stirred with 50 ml. of water, filtered, washed with water, and dried. Trituration of the dried filter cake with isopropyl alcohol yields 5.3 g. (95%) of N-(4-nitrostyryl)-4-aminobenzamidine free base, m.p. 195°-197° C. (dec.) The free base (5.0 g.) dissolved in 400 ml. of hot 1:1 methanolacetone and acidified with ethanolic hydrogen chloride provides 3.5 g. of analytically pure 4-AMINO-N-(4-NITROSTYRYL)BENZAMIDINE HYDROCHLORIDE as a yellow solid, m.p. 247°-248° C. (dec.)(corr.) Concentration of the mother liquors and trituration of the residue provided an additional 2.6 g. of the hydrochloride salt.

Workup

  1. customConcentration of the reaction mixture affords a residue which
  2. filtrationof water, filtered
  3. washwashed with water
  4. customdried
  5. filtrationTrituration of the dried filter cake with isopropyl alcohol
  6. customyields 5.3 g
  7. customprovides 3.5 g

Sources & evidence

ORD record
ord-a6ceab6e97074ecfac39cc07c7f5acf3
Source dataset
uspto-grants-1978_06
Patent number
US04096183

Reaction notes

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