Pyridine → HCID 54333333, compound

HRID 2286156Notes

Reaction equation

HRID 2286156 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH3:11])=[O:9].C(Cl)Cl.[CH3:15][NH:16][S:17]([Cl:20])(=[O:19])=[O:18]>O>[CH3:11][O:10][C:8]([N:16]([CH3:15])[S:17]([Cl:20])(=[O:19])=[O:18])=[O:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 54333333HCID 54333333, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

158.2 parts of pyridine are added at -10° C., while stirring, to a solution of 188.8 parts of methyl chloroformate in 1,200 parts of methylene chloride. Then 259.2 parts of methylsulfamic acid chloride are added at the same temperature while stirring, and the mixture is stirred for half an hour at 0° C. and for one hour at 25° C. The reaction mixture is then stirred for 6 minutes with 600 parts of water at 5° C. and pH 1. The organic phase is then separated off from the 2-phase mixture formed, and is filtered and subjected to fractional distillation. 341 parts (91% of theory) of N-methoxycarbonyl-N-methylsulfamic acid chloride, of boiling point 49°-51° C./0.13 mbar and nD25 =1.4600, are obtained.

Workup

  1. stirringthe mixture is stirred for half an hour at 0° C. and for one hour at 25° C
  2. customThe organic phase is then separated off from the 2-phase mixture
  3. customformed
  4. filtrationis filtered
  5. distillationsubjected to fractional distillation

Sources & evidence

ORD record
ord-c86433a3edb9417fb64521bae54bd053
Source dataset
uspto-grants-1982_04
Patent number
US04327034

Reaction notes

Loading…