Chloride → Cyclohexanecarboxamide, N-(4-(cyanomethyl)phenyl)-5-methyl-2-(1-methylethyl)-

HRID 444604Notes

Reaction equation

HRID 444604 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.N1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[OH2:18]>>[C:7]([CH2:6][C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:12]([CH:13]2[CH:4]([CH:5]([CH3:9])[CH3:6])[CH2:3][CH2:2][CH:15]([CH3:16])[CH2:14]2)=[O:18])=[CH:3][CH:4]=1)#[N:8]

Participants

5

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 1049PyridineHCID 770004-Aminophenylacetonitrile

Product 1

HCID 25113851Cyclohexanecarboxamide, N-(4-(cyanomethyl)phenyl)-5-methyl-2-(1-methylethyl)-

Procedure

To a flask, were added 6.6 g (50 mmol) of 4-aminobenzyl cyanide, 4.04 mL of pyridine and 100 mL MtBE. To this mixture, 10 g of p-menthane-3-carbon*yl chloride were added dropwise over 5 minutes. The reaction mixture was stirred for 24 h. To the reaction mixture, 50 mL of water were added. The mixture was separated. The organic layer was washed with 50 mL of water and 50 mL of brine. The organic layer was dried over MgSO4. The solvent was evaporated in vacuo to afford the crude product, which was recrystallized from hexanes to afford 10.1 g of the desired product with the following spectroscopic properties:

Workup

  1. customThe mixture was separated
  2. washThe organic layer was washed with 50 mL of water and 50 mL of brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customThe solvent was evaporated in vacuo
  5. customto afford the crude product, which
  6. customwas recrystallized from hexanes

Sources & evidence

ORD record
ord-b02e27fc945948d4979a75e5b131dc9b
Source dataset
uspto-grants-2013_07
Patent number
USRE044339E1

Reaction notes

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