Triethylamine → 2-Methyl-2-methylsulfonylpropionaldoxime N-chloroacetyl-N-methylcarbamate

HRID 482917Notes

Reaction equation

HRID 482917 reaction equation
[Cl:1][CH2:2][C:3]([N:5]([CH3:9])[C:6](Cl)=[O:7])=[O:4].[CH3:10][C:11]([S:16]([CH3:19])(=[O:18])=[O:17])([CH3:15])[CH:12]=[N:13][OH:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:10][C:11]([S:16]([CH3:19])(=[O:18])=[O:17])([CH3:15])[CH:12]=[N:13][OH:14].[Cl:1][CH2:2][C:3]([N:5]([CH3:9])[C:6](=[O:14])[O-:7])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5189322-Methyl-2-(methylsulfonyl)propionaldehyde oximeHCID 13424133N-chloroacetyl-N-methylcarbamoyl chloride

Product 1

HCID 867406792-Methyl-2-methylsulfonylpropionaldoxime N-chloroacetyl-N-methylcarbamateYield 125.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 5.0 g (0.029 m) of N-chloroacetyl-N-methylcarbamoyl chloride dissolved in 40 ml of toluene was added 4.74 g (0.029 m) of 2-methyl-2-methylsulfonylpropionaldoxime dissolved in 35 ml. of toluene followed by a slow addition of 2.9 g (0.029 m) of triethylamine. The reaction mixture was stirred at ambient temperatures over a period of 3 days. The solid product was filtered. The filter cake was washed with water and hexane and air dried to afford 5.7 g of a white solid with a melting point of 120°-121° C.

Workup

  1. dissolutiondissolved in 35 ml
  2. filtrationThe solid product was filtered
  3. washThe filter cake was washed with water and hexane and air
  4. customdried

Sources & evidence

ORD record
ord-464a23a65dff490e9ee023c67d514181
Source dataset
uspto-grants-1986_03
Patent number
US04576965

Reaction notes

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