Acetonitrile → 3-methyl-4-(alpha-phenoxypropionamido)phenyl N-methylcarbamate

HRID 2072429Notes

Reaction equation

HRID 2072429 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(CC)CC)C.C(#N)C.[O:24]([CH:31]([CH3:35])[C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C.O.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:32](=[O:33])[CH:31]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:35])=[C:7]([CH3:12])[CH:6]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 25072AminomatacilHCID 954362-Phenoxypropanoyl chloride

Product 1

HCID 214092763-methyl-4-(alpha-phenoxypropionamido)phenyl N-methylcarbamate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-methyl-4-aminophenyl N-methylcarbamate (1.8g., 0.01 mole), triethylamine (1.31g., 0.013 mole), and a solvent mixture of acetonitrile (20 ml.) and benzene (20 ml.) was stirred while a benzene solution of α-phenoxypropionyl chloride was added dropwise. The resulting mixture was refluxed for a short time, cooled, and solvents removed under reduced pressure to yield a tacky residue. This residue was dissolved in a minimum of hot 50% aqueous ethanol. Addition of more water and cooling produced a white precipitate of the desired product (3 grams, m.p. 123°-25° C.).

Workup

  1. additionwas added dropwise
  2. temperatureThe resulting mixture was refluxed for a short time
  3. temperaturecooled
  4. customsolvents removed under reduced pressure
  5. customto yield a tacky residue
  6. temperaturecooling

Sources & evidence

ORD record
ord-c8714b58b3d64a8b9e04b85548367856
Source dataset
uspto-grants-1977_09
Patent number
US04051254

Reaction notes

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