Water → phenyl N-(2,4-difluorophenyl)carbamate

HRID 387879Notes

Reaction equation

HRID 387879 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].O>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:17](=[O:18])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 15891Phenyl chloroformate

Product 1

HCID 13733129phenyl N-(2,4-difluorophenyl)carbamateYield 85.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 2,4-difluoroaniline (10 ml, 98.21 mmol) in tetrahydrofuran (200 ml), pyridine (8.7 ml, 108.33 mmol) was added at room temperature and the mixture was stirred. It was then cooled on ice, phenyl chloroformate (13.6 ml, 108.33 mmol) was added dropwise over 15 minutes, and the mixture was then stirred at room temperature for 24 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate and tetrahydrofuran, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the filtrate was distilled off under reduced pressure. The obtained crystals were suspended in ethanol and diluted with hexane, and then the crystals were filtered out, washed with hexane and dried by aspiration to obtain the title compound (21.00 g, 84.26 mmol, 85.80%) as light violet crystals.

Workup

  1. additionwas added at room temperature
  2. additionwas added dropwise over 15 minutes
  3. stirringthe mixture was then stirred at room temperature for 24 hours
  4. washthe extract was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe filtrate was distilled off under reduced pressure
  7. additiondiluted with hexane
  8. filtrationthe crystals were filtered out
  9. washwashed with hexane
  10. customdried by aspiration

Sources & evidence

ORD record
ord-9d17b6e4e11842e59c50ae4755b0c543
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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