Pyridine → Propan-2-yl [2-iodo-4-methyl-5-(trifluoromethyl)phenyl]carbamate

HRID 507039Notes

Reaction equation

HRID 507039 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[I:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[NH2:20].N1C=CC=CC=1>ClCCl>[I:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]([F:18])([F:19])[F:17])=[CH:11][C:10]=1[NH:20][C:2](=[O:3])[O:4][CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 534211462-Iodo-4-methyl-5-(trifluoromethyl)aniline

Product 1

HCID 59432461Propan-2-yl [2-iodo-4-methyl-5-(trifluoromethyl)phenyl]carbamateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add a solution of isopropyl chloroformate (99.6 mL, 99.6 mmol, 1M in toluene) dropwise to a solution of 2-iodo-4-methyl-5-trifluoromethylphenylamine (27.26 g, 90.55 mmol) and pyridine (14.6 mL, 181.1 mmol) in dichloromethane (350 mL) at 5° C. under an atmosphere of nitrogen and warm the mixture to room temperature. Stir for 3 h and wash the mixture with 2 N HCl (100 mL) and brine (100 mL). Dry over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as a tan solid (33.59 g, 96%), which is used in the next step without purification. APCI MS m/z 388 (M+H)+.

Workup

  1. washwash the mixture with 2 N HCl (100 mL) and brine (100 mL)
  2. dry with materialDry over anhydrous sodium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-349cbcbcdaf84f9bab55a05cebc7af8c
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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