Reaction #969897

ord-2d6f4484f9314edbbd2af6e7144af055

Reaction equation

CN(C)C=O
Dimethylformamide
COc1ccc(N)c(S(=O)(=O)O)c1
2-amino-5-methoxybenzenesulphonic acid
O=S(Cl)Cl
thionyl chloride
→
COc1ccc(NC=[N+](C)C)c(S(=O)(=O)Cl)c1.[Cl-]
title product
COc1ccc(NC=[N+](C)C)c(S(=O)(=O)Cl)c1.[Cl-]
N-[[[2-(chlorosulphonyl)-4-methoxyphenyl]amino]methylene]-N-methyl-methanaminium chloride

Reactants

CN(C)C=O
Dimethylformamide
COc1ccc(N)c(S(=O)(=O)O)c1
2-amino-5-methoxybenzenesulphonic acid
O=S(Cl)Cl
thionyl chloride

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureis maintained at that temperature for 1.5 hours
  2. 2
    TemperatureAfter cooling
  3. 3
    Otherthe stirred reaction solution
  4. 4
    OtherA precipitate is formed which
  5. 5
    Filtrationis rapidly filtered off
  6. 6
    Washrinsed with toluene
  7. 7
    Dryingdried at 40° C. in vacuo in the presence of KOH pellets

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08236790B2uspto-grants-2012_08