Triethylamine → 1-chloro-1-methyl-2-(N-methyl-N-cyclohexylcarbamoyloxy)-2-methoxyiminoethane

HRID 1578604Notes

Reaction equation

HRID 1578604 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:8])[CH:5]([Cl:7])[CH3:6].C(N(CC)CC)C.[CH3:16][N:17]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:18](Cl)=[O:19]>C1C=CC=CC=1>[Cl:7][CH:5]([CH3:6])[C:4]([O:8][C:18](=[O:19])[N:17]([CH3:16])[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[N:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15209947N-cyclohexyl-N-methylcarbamoyl chlorideHCID 215595642-Chloro-N-methoxypropanamide

Product 1

HCID 545197281-chloro-1-methyl-2-(N-methyl-N-cyclohexylcarbamoyloxy)-2-methoxyiminoethane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

N-Methoxy-α-chloropropionamide (13.8 grams; 0.1 mole), benzene (70 ml) and triethylamine (12 grams; 0.12 mole) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. N-Methyl-N-cyclohexylcarbamoyl chloride (17.9 grams; 0.1 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 3 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-1-methyl-2-(N-methyl-N-cyclohexylcarbamoyloxy)-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 3 hours
  7. distillationAfter this time the reaction mixture is distilled
  8. customto remove benzene

Sources & evidence

ORD record
ord-26f93534987b46019f3418badb09d0bd
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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