Diphosgene → HCID 18372247, compound

HRID 2301267Notes

Reaction equation

HRID 2301267 reaction equation
[Cl:1][C:2]([O:4]C(Cl)(Cl)Cl)=O.[CH3:9][N:10]([CH3:22])[S:11]([C:14]1[S:18][C:17]([NH:19][CH3:20])=[N:16][C:15]=1[CH3:21])(=[O:13])=[O:12]>O1CCOCC1>[CH3:9][N:10]([CH3:22])[S:11]([C:14]1[S:18][C:17]([N:19]([CH3:20])[C:2]([Cl:1])=[O:4])=[N:16][C:15]=1[CH3:21])(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 18372251N,N,4-Trimethyl-2-(methylamino)-1,3-thiazole-5-sulfonamide

Product 1

HCID 18372247HCID 18372247, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

15.4 g (78 mmol) of trichloromethyl chloroformate (“diphosgene”) were added at room temperature to a solution of 22.9 g (97 mmol) of N,N,4-trimethyl-2-(methyl-amino)-1,3-thiazole-5-sulphonamide in 360 ml of dioxane, and the mixture was heated to reflux until a homogeneous solution was obtained, and TLC showed that no starting material remained. After removal of the solvent in vacuo, 29.0 g of the product were obtained in the form of an oil. (Yield 100%, NMR (CDCl3): 3.89 (3H), 2.81 (6H), 2.62 (3H) ppm).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux until a homogeneous solution
  3. customwas obtained
  4. customAfter removal of the solvent in vacuo

Sources & evidence

ORD record
ord-fd0aba94ef1947278fa3249f414244e6
Source dataset
uspto-grants-2002_12
Patent number
US06500817B1

Reaction notes

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