4-Nitrobenzenesulfonyl chloride → N-(Cyanomethyl)-4-nitrobenzenesulfonamide

HRID 1906374Notes

Reaction equation

HRID 1906374 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].[OH-].[Na+].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9]>O>[C:4]([CH2:3][NH:2][S:17]([C:14]1[CH:13]=[CH:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:16][CH:15]=1)(=[O:18])=[O:19])#[N:5]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 3113405N-(Cyanomethyl)-4-nitrobenzenesulfonamideYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 27.8 g (0.3 moles) aminoacetonitrile hydrochloride in 200 ml water, 24 g (0.3 moles) sodium hydroxide (50% aqueous) were added. The resulting mixture was cooled to about 20° C. with an ice bath. The ice bath was removed; then 22.2 g (0.1 mole) 4-nitrobenzenesulfonyl chloride were added. The reaction mixture was stirred 18 hours at ambient temperature. The solids were filtered. The resulting wet cake was crystallized from 50 ml ethanol. The solids were dried in vacuo to give 17.5 g of the above-identified product as a dark-yellow solid, melting point 115°-120° C.

Workup

  1. customThe ice bath was removed
  2. filtrationThe solids were filtered
  3. customThe resulting wet cake was crystallized from 50 ml ethanol
  4. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-b177908c9c3942a5b0e4ec6a6f7c9ae2
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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