2-chloro-N-methoxyacetamide → 1-chloro-2-[N-(2-methyl-4-methylthiophenyl)carbamoyloxy]-2-methoxyiminoethane

HRID 1578598Notes

Reaction equation

HRID 1578598 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:7])[CH2:5][Cl:6].[CH3:8][C:9]1[CH:14]=[C:13]([S:15][CH3:16])[CH:12]=[CH:11][C:10]=1[N:17]=[C:18]=[O:19]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1C=CC=CC=1>[Cl:6][CH2:5][C:4]([O:7][C:18](=[O:19])[NH:17][C:10]1[CH:11]=[CH:12][C:13]([S:15][CH3:16])=[CH:14][C:9]=1[CH3:8])=[N:3][O:2][CH3:1]

Participants

5

Reactant 2

HCID 127743452-chloro-N-methoxyacetamideHCID 215595952-Methyl-4-methylthiophenylisocyanate

Product 1

HCID 737960341-chloro-2-[N-(2-methyl-4-methylthiophenyl)carbamoyloxy]-2-methoxyiminoethane

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 241BenzeneSolvent2×

Procedure

N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (60 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Methyl-4-methylthiophenylisocyanate (21.5 grams; 0.12 mole) dissolved in benzene (30 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 2 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-[N-(2-methyl-4-methylthiophenyl)carbamoyloxy]-2-methoxyiminoethane.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionis incrementally added to the reaction mixture
  4. additionAfter the addition
  5. temperatureis heated
  6. temperatureat reflux for a period of about 2 hours
  7. distillationAfter this time the reaction mixture is distilled
  8. customto remove benzene

Sources & evidence

ORD record
ord-66b16a99454f455fb7071e61193d1fbd
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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