Potassium Carbonate → Phenyl 4-methoxy-3-(trifluoromethyl)phenylcarbamate

HRID 631445Notes

Reaction equation

HRID 631445 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[C:10]([F:13])([F:12])[F:11].C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:5][C:4]=1[C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 6007055-Amino-2-methoxybenzotrifluoride

Product 1

HCID 66876756Phenyl 4-methoxy-3-(trifluoromethyl)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxy-3-trifluoromethyl aniline (500 mg, 2.62 mmol) in 20 mL of tetrahydrofuran was added potassium carbonate (470 mg, 3.4 mmol), followed by phenyl chloroformate (532 mg, 3.4 mmol). This solution was stirred overnight at room temperature, then concentrated and purified by silica gel chromatography using a gradient of ethyl acetate/hexanes 0-20% to afford phenyl 4-methoxy-3-(trifluoromethyl)phenylcarbamate as a white solid. 1H NMR (300 MHz, CDCl3) 7.75-7.65 (m, 2H), 7.60-7.40 (m, 2H), 7.27-7.19 (m, 3H), 7.00-6.93 (m, 2H), 3.89 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-0f27655085ac4e9e87a7c3fbf854d704
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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