Potassium Carbonate → Phenyl 3-(2-cyanopropan-2-yl)phenylcarbamate

HRID 871654Notes

Reaction equation

HRID 871654 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>C1COCC1>[C:9]([C:8]([C:4]1[CH:3]=[C:2]([NH:1][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][CH:5]=1)([CH3:12])[CH3:11])#[N:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 569657872-(3-Aminophenyl)-2-methylpropanenitrile

Product 1

HCID 66877200Phenyl 3-(2-cyanopropan-2-yl)phenylcarbamateYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3-aminophenyl)-2-methylpropanenitrile (490 mg, 3.06 mmol) and potassium carbonate (552 mg, 4 mmol) in anhydrous THF (4.2 ml) was added dropwise phenyl chloroformate (0.81 ml, 6.4 mmol) as a solution in THF (2 ml). The reaction mixture was stirred at rt overnight. The solvent was removed and the residue taken in DCM, washed with water and brine and the organics combined, dried (MgSO4) and concentrated. The crude was purified by silica gel chromatography (hexane/ethyl acetate 15%) to afford phenyl 3-(2-cyanopropan-2-yl)phenylcarbamate (828 mg, 96%) as a solid. 1H NMR (300 MHz, CDCl3) δ 1.72 (s, 6H), 7.20-7.28 (m, 4H), 7.35-7.41 (m, 4H), 7.65 (s, 1H); LC-MS (ESI) m/z 281 (M+H)+.

Workup

  1. customThe solvent was removed
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel chromatography (hexane/ethyl acetate 15%)

Sources & evidence

ORD record
ord-0ce77a357e60432481709bee0eedf889
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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