18-Crown-6 → N-chloroacetyl-N-methylcarbamoyl fluoride

HRID 980429Notes

Reaction equation

HRID 980429 reaction equation
[Cl:1][CH2:2][C:3]([N:5]([CH3:9])[C:6](Cl)=[O:7])=[O:4].[F-:10].[K+].C1OCCOCCOCCOCCOCCOC1>ClCCl>[Cl:1][CH2:2][C:3]([N:5]([CH3:9])[C:6]([F:10])=[O:7])=[O:4]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 13424133N-chloroacetyl-N-methylcarbamoyl chloride

Product 1

HCID 13772937N-chloroacetyl-N-methylcarbamoyl fluorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10.0 g of N-Chloroacetyl-N-methylcarbamoyl chloride, 3.8 g of anhydrous potassium fluoride and 0.5 g of 18-crown-6 in 50 cc of dichloromethane was stirred at room temperature under nitrogen for about 16 hours. The liquid was decanted and the residue was extracted with 50 cc dichlormethane. The dichloromethane layers were combined and the solvent stripped off to afford 9.0 g. (Yield 100%) of N-chloroacetyl-N-methylcarbamoyl fluoride. The product was further purified by distillation under reduced pressure. B.p. 59° C./0.2 mm.

Workup

  1. customThe liquid was decanted
  2. extractionthe residue was extracted with 50 cc dichlormethane
  3. customto afford 9.0 g

Sources & evidence

ORD record
ord-004ef200fc5841ada6f0de7397b9b257
Source dataset
uspto-grants-1987_01
Patent number
US04637901

Reaction notes

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