Dimethylformamide → N-[[[2-(chlorosulphonyl)-4-methoxyphenyl]amino]methylene]-N-methyl-methanaminium chloride

HRID 882715Notes

Reaction equation

HRID 882715 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[S:15]([OH:18])(=O)=[O:16].S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl-:21].[Cl:21][S:15]([C:8]1[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=1[NH:6][CH:3]=[N+:2]([CH3:5])[CH3:1])(=[O:18])=[O:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 832602-Amino-5-methoxybenzenesulfonic acid

Product 1

HCID 86645616N-[[[2-(chlorosulphonyl)-4-methoxyphenyl]amino]methylene]-N-methyl-methanaminium chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Dimethylformamide (0.152 mol) is added dropwise to a suspension of 2-amino-5-methoxybenzenesulphonic acid (0.152 mol) in thionyl chloride (0.763 mol). The reaction mixture is heated very gradually to 70° C. and is maintained at that temperature for 1.5 hours. After cooling, the stirred reaction solution is treated by the addition of 20 ml of toluene. A precipitate is formed which is rapidly filtered off, rinsed with toluene and then dried at 40° C. in vacuo in the presence of KOH pellets, to yield the title product.

Workup

  1. temperatureis maintained at that temperature for 1.5 hours
  2. temperatureAfter cooling
  3. customthe stirred reaction solution
  4. customA precipitate is formed which
  5. filtrationis rapidly filtered off
  6. washrinsed with toluene
  7. dry with materialdried at 40° C. in vacuo in the presence of KOH pellets

Sources & evidence

ORD record
ord-2d6f4484f9314edbbd2af6e7144af055
Source dataset
uspto-grants-2012_08
Patent number
US08236790B2

Reaction notes

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