Acetonitrile → 3-methyl-4-(methoxyacetamido)phenyl N-methylcarbamate

HRID 2072426Notes

Reaction equation

HRID 2072426 reaction equation
[CH3:1][NH:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([CH3:12])[CH:6]=1.C(#N)C.C(N(CC)CC)C.[CH3:24][O:25][CH2:26][C:27](Cl)=[O:28]>C1C=CC=CC=1>[CH3:1][NH:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:27](=[O:28])[CH2:26][O:25][CH3:24])=[C:7]([CH3:12])[CH:6]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 25072AminomatacilHCID 96623Methoxyacetyl chloride

Product 1

HCID 543602023-methyl-4-(methoxyacetamido)phenyl N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

3-methyl-4-aminophenyl N-methylcarbamate (3.6g. 0.02 mole) was dissolved in 35 ml. of benzene and 25 ml. of acetonitrile along with triethylamine (2.23g., 0.022 mole). To this stirred solution was added dropwise a solution of methoxyacetyl chloride in benzene. An exotherm to 45° C. was noted as solids began to form. Further heating at reflux for one hour yielded 2.4g. of Et3N.HCl upon filtration. Solvent removal from the filtrate under reduced pressure gave a product which was recrystallized from ethanol-water. The tan solid (2.4g.) melted at 129.5°-132° C. and the infrared spectrum (KBr) displayed the characteristic double carbonyl (5.7 μ and 5.95 μ).

Workup

  1. customto 45° C.
  2. customto form
  3. temperatureFurther heating
  4. temperatureat reflux for one hour
  5. customyielded 2.4g
  6. filtrationof Et3N.HCl upon filtration
  7. customSolvent removal from the filtrate under reduced pressure
  8. customgave a product which
  9. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-5a59fd0ded35404fa0b0549b3840a1dd
Source dataset
uspto-grants-1977_09
Patent number
US04051254

Reaction notes

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