Methanol → N-(3-amino-4-chlorophenyl)methanesulfonamide

HRID 2295250Notes

Reaction equation

HRID 2295250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH2:9].CO.[CH3:12][S:13](Cl)(=[O:15])=[O:14].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:13]([CH3:12])(=[O:15])=[O:14])=[CH:4][C:3]=1[NH2:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 212094-Chloro-M-phenylenediamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 16777591N-(3-amino-4-chlorophenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

35.8 g of 4-chloro-1,3-diaminobenzene are stirred thoroughly into 250 ml of water and 50 ml of methanol. 23 ml of methanesulphonyl chloride are added dropwise at 0° C. in the course of about 2 hours; the pH is kept at 4 by dropwise addition of concentrated sodium hydroxide solution. The mixture is subsequently stirred at room temperature for about 2 hours and, if appropriate after diluting with water, the 1-chloro-2-amino-4-methanesulphonamido-benzene which has separated out is then filtered off. It is sufficiently pure for further reactions according to Example 59.

Workup

  1. customthe 1-chloro-2-amino-4-methanesulphonamido-benzene which has separated out
  2. filtrationis then filtered off

Sources & evidence

ORD record
ord-45b862891617423a8765fa31b8458d87
Source dataset
uspto-grants-1984_01
Patent number
US04424156

Reaction notes

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