Potassium Carbonate → HCID 66876621, compound

HRID 871440Notes

Reaction equation

HRID 871440 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20].CN(C1C=CC=CN=1)C>CCOC(C)=O.C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([NH:8][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 218852-DimethylaminopyridineHCID 793343-tert-Butylaniline

Product 1

HCID 66876621HCID 66876621, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To THF (15 mL) was added 3-tert-butylaniline (447 mg, 3 mmol), potassium carbonate (828 mg, 6 mmol), phenyl chloroformate (1.13 mL, 9 mmol), and dimethylaminopyridine (36 mg, 0.30 mmol) and the reaction 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-tert-butylphenylcarbamate (458 mg, 1.70 mmol, 57%). 1H NMR (300 MHz, DMSO-d6) δ 10.14 (s, 1H), 7.59 (s, 1H), 7.49-7.10 (m, 7H), 7.08 (d, 1H), 1.25 (s, 9H); LC-MS (ESI) m/z 270 (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-ff53eb5ef979493f83a36ca28e1c0247
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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