Tetrahydrofuran → HCID 66876449, compound

HRID 871432Notes

Reaction equation

HRID 871432 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[NH2:11].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:11][C:26](=[O:27])[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 6056715-(Trifluoromethyl)-m-anisidine

Product 1

HCID 66876449HCID 66876449, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To THF was added 3-methoxy-5-(trifluoromethyl)aniline (1.10 g, 5.7 mmol), potassium carbonate (2 equivalents), phenyl chloroformate (3 equivalents) and 4-dimethylaminopyridine (0.1 equivalent) and the reaction was stirred at room temperature overnight. The mixture was diluted with EtOAc, filtered, concentrated in vacuo, and purified by silica gel column chromatography (5-15% EtOAc/hexanes) to give phenyl 3-methoxy-5-(trifluoromethyl)phenylcarbamate (1.02 g, 3.28 mmol, 57%). 1H NMR (300 MHz, DMSO-d6) δ 10.59 (s, 1H), 7.50-7.35 (m, 4H), 7.31-7.22 (m, 3H), 6.94 (s, 1H), 3.81 (s, 3H); LC-MS (ESI) m/z 312 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel column chromatography (5-15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a7e936a2f5514d1bbf988085638581e4
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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