Hydrochloric Acid → 4-Hydrazino-N-methylbenzenemethanesulfonamide hydrochloride

HRID 1194754Notes

Reaction equation

HRID 1194754 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][S:13]([NH:16][CH3:17])(=[O:15])=[O:14])=[CH:8][CH:7]=1.[ClH:18]>O>[ClH:18].[NH:5]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][S:13]([NH:16][CH3:17])(=[O:15])=[O:14])=[CH:8][CH:7]=1)[NH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 27781314-Amino-N-methylbenzenemethanesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 142342634-Hydrazino-N-methylbenzenemethanesulfonamide hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (13.72 g) in water (160 ml) was added slowly to a cooled stirred mixture of 4-Amino-N-methylbenzene methanesulphonamide (39.3 g), water (240 ml) and conc. hydrochloric acid (400 ml) such that the temperature did not exceed 0°. After stirring for 15 min this mixture was added slowly to a cold solution of stannous chloride dihydrate (221.1 g) in conc. hydrochloric acid (400 ml) again keeping the temperature below 0°. Once the addition was complete the mixture was allowed to warm to room temperature (1 h). The solid was collected by filtration, washed well with diethyl ether (4×250 ml) and dried at 45° to give the title compound as a white powder (31.6 g). An assay by periodate titration showed this to be 91.3% pure.

Workup

  1. customdid not exceed 0°
  2. stirringAfter stirring for 15 min this mixture
  3. customthe temperature below 0°
  4. additionOnce the addition
  5. filtrationThe solid was collected by filtration
  6. washwashed well with diethyl ether (4×250 ml)
  7. customdried at 45°

Sources & evidence

ORD record
ord-a389fc6c04104ce588477eb4ba7dc5b3
Source dataset
uspto-grants-1989_03
Patent number
US04816470

Reaction notes

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