Phosgene → HCID 85890678, compound

HRID 596924Notes

Reaction equation

HRID 596924 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[Cl:12][C:13]([Cl:17])([Cl:16])[S:14]Cl.[C:18](Cl)([Cl:20])=[O:19]>C(#N)C>[Cl:12][C:13]([Cl:17])([Cl:16])[S:14][N:4]([CH2:1][CH2:2][CH3:3])[C:18]([Cl:20])=[O:19]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 7852PropylamineHCID 8471TriethylamineHCID 11666Trichloromethanesulfenyl chloride

Product 1

HCID 85890678HCID 85890678, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 59.1 g (1 mol) N-propylamine and 101.2 g (1 mol) triethylamine in 200 ml acetonitrile was added dropwise to a solution of 185.9 g (1 mol) of trichloromethylsulfenyl chloride in 1 liter of acetonitrile at about 0°-5° C over a 1-hour period. Into the reaction mixture was then added 98.9 g (1 mol) phosgene over a 1-hour period. The reaction was stirred at about 25° C for about 16 hours. The solvent was evaporated under reduced pressure, and the residue was extracted with hexane. The hexane extracts were evaporated under reduced pressure to give a dark oil. The oil was distilled through a short column to give 22 g of the carbamoyl chloride product, b.p. 71°-81° C at 0.75 mm Hg.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with hexane
  3. customThe hexane extracts were evaporated under reduced pressure
  4. customto give a dark oil
  5. distillationThe oil was distilled through a short column

Sources & evidence

ORD record
ord-7bf1e3b74a1c4c3a84aadc41c549ae34
Source dataset
uspto-grants-1977_03
Patent number
US04012436

Reaction notes

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