Pyridine → Phenyl (3-chloro-4-(trifluoromethyl)phenyl)carbamate

HRID 2371128Notes

Reaction equation

HRID 2371128 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[C:19]([F:22])([F:21])[F:20])[NH2:15].N1C=CC=CC=1>C1COCC1.C(OCC)(=O)C.Cl>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:17][C:18]=1[C:19]([F:21])([F:22])[F:20]

Participants

7

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 679623-Chloro-4-(trifluoromethyl)aniline

Product 1

HCID 57656832Phenyl (3-chloro-4-(trifluoromethyl)phenyl)carbamate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenyl chloroformate (0.86 mL) was added slowly to a stirring solution of 3-chloro-4-trifluoromethyl aniline (933 mg) in THF (10 mL) containing pyridine (1.07 mL) under an argon atmosphere. The reaction was stirred for 18 h then diluted with ethyl acetate (35 mL) and 1M HCl (20 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 then dried (MgSO4), filtered and evaporated. Trituration with 1:9 EtOAc:isohexanes (10 mL) at reflux followed by cooling to RT afforded a solid which was filtered to afford 1.15 g of the title compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. temperatureTrituration with 1:9 EtOAc:isohexanes (10 mL) at reflux
  7. customafforded a solid which
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-ec54f003e63d4ea284bd8a0ab11421ff
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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