Methanol → Ethyl hydrogen (3-fluorophenyl)carbonimidate

HRID 461402Notes

Reaction equation

HRID 461402 reaction equation
CO.[F:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].C(N(CC)CC)C.ClN[C:20](=[O:24])[O:21][CH2:22][CH3:23]>C1C=CC=CC=1.O>[F:3][C:4]1[CH:5]=[C:6]([NH:7][C:20](=[O:24])[O:21][CH2:22][CH3:23])[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 97423-FluoroanilineHCID 11829582ethyl chlorocarbamate

Product 1

HCID 223116Ethyl hydrogen (3-fluorophenyl)carbonimidateYield 34.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

The mixture of 150 ml of methanol, 25 g of m-fluoroaniline, 30 g of triethylamine and 32.5 g of ethyl chlorocarbamate was heated under reflux condition. After the completion of the reaction, the solvent was evaporated under reduced pressure to obtain the residue, to which was added 100 ml of water and 100 ml of benzene. The benzene layer was separated, washed twice with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain the residue, which was distilled under reduced pressure, and there was obtained 12.5 g (yield 34.8%) of ethyl m-fluorophenylcarbamate as colourless oil having a boiling point of 102° C/1.5 mmHg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux condition
  3. customAfter the completion of the reaction
  4. customthe solvent was evaporated under reduced pressure
  5. customto obtain the residue
  6. customThe benzene layer was separated
  7. washwashed twice with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. customto obtain the residue, which
  11. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-16591ae1c8ae4d7d9bcbcf4496cd3788
Source dataset
uspto-grants-1977_12
Patent number
US04062862

Reaction notes

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