Sodium Hydroxide → p-Aminobenzamidine

HRID 1706074Notes

Reaction equation

HRID 1706074 reaction equation
[OH-].[Na+].Cl.[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[NH:10])=[CH:7][CH:6]=1>O>[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[NH:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 122765Benzenecarboximidamide, 4-amino-, hydrochloride (1:1)

Product 1

HCID 1725p-Aminobenzamidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 3 N hydrochloric 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.

Sources & evidence

ORD record
ord-a605efeb704b45df94bf2d2b0f460276
Source dataset
uspto-grants-1980_06
Patent number
US04206142

Reaction notes

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