Water → alpha-Cyano-N-(2,4,6-trimethoxyphenyl)benzene acetamide

HRID 264131Notes

Reaction equation

HRID 264131 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:15]=1[N:24]=[C:25]=[O:26].O>CN(C)C=O>[C:8]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:25]([NH:24][C:15]1[C:16]([O:22][CH3:23])=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=1[O:13][CH3:12])=[O:26])#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 100818122,4,6-Trimethoxyphenyl isocyanate

Product 1

HCID 10496352alpha-Cyano-N-(2,4,6-trimethoxyphenyl)benzene acetamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenylacetonitrile (2.64 mL, 22.8 mol) was added dropwise to an ice-cooled solution of sodium hydride (0.91 g, 22.8 mmol) in dimethyl formamide (50 mL), and the mixture stirred for 15 minutes while allowing to warm to room temperature. 2,4,6-Trimethoxyphenylisocyanate (4.78 g, 22.8 mmol) was added portionwise over 2 minutes, and then the mixture was stirred vigorously for 0.5 hour and poured into water (200 mL). The solid obtained was washed with water (100 mL) and taken up in chloroform (1 L). The organic layer was separated and dried with MgSO4, filtered, and concentrated to yield a pale purple solid (6.13 g, 82%). %(found): C, 65.94; H, 5.56; N, 8.10.

Workup

  1. stirringthe mixture was stirred vigorously for 0.5 hour
  2. customThe solid obtained
  3. washwas washed with water (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8c3a714226ed49888d899ab28833d55e
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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