Potassium Carbonate → HCID 66876621, compound

HRID 1917839Notes

Reaction equation

HRID 1917839 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-669c78806e314c12bdeb20c19a249e0d
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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