Pyridine → HCID 54327741, compound

HRID 2286155Notes

Reaction equation

HRID 2286155 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH3:11])=[O:9].[CH:12]([NH:15][S:16]([Cl:19])(=[O:18])=[O:17])([CH3:14])[CH3:13].C(Cl)Cl>O>[CH3:11][O:10][C:8]([N:15]([CH:12]([CH3:14])[CH3:13])[S:16]([Cl:19])(=[O:18])=[O:17])=[O:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 117737Isopropylsulphamoyl chloride

Product 1

HCID 54327741HCID 54327741, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

39.6 parts of pyridine are added in the course of 15 minutes at 10° C., whilst stirring, to a mixture of 47.2 parts of methyl chloroformate and 78.8 parts of isopropylsulfamic acid chloride in 330 parts of methylene chloride. The reaction mixture is then stirred for 10 minutes at 22° C. Thereafter, the mixture is stirred for 8 minutes with 350 parts of water at 6° 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. 72.1 parts (67% of theory) of N-methoxycarbonyl-N-isopropylsulfamic acid chloride, of boiling point 60°-64° C./0.13 mbar and nD25 =1.4540, are obtained.

Workup

  1. customThe organic phase is then separated off from the 2-phase mixture
  2. customformed
  3. filtrationis filtered
  4. distillationsubjected to fractional distillation

Sources & evidence

ORD record
ord-982bbb867b7e4963818dad69381b7a1f
Source dataset
uspto-grants-1982_04
Patent number
US04327034

Reaction notes

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