p-Toluidine → HCID 67132143, compound

HRID 244992Notes

Reaction equation

HRID 244992 reaction equation
C[Si]([C:5]#[N:6])(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[Cl:15][CH2:16][C:17]([CH2:19][Cl:20])=O>C(OCC)(=O)C>[Cl:15][CH2:16][C:17]([CH2:19][Cl:20])([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 107931,3-DichloroacetoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 67132143HCID 67132143, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Trimethylsilyl cyanide (0.27 ml, 2 mmol) was added dropwise to a mixture of p-toluidine (0.107 g, 1 mmol) and 1,3-dichloroacetone (0.254 g, 2 mmol). The reaction mixture was heat to 80° C. and stirred for 6 h. To the mixture was added 20 ml of ethyl acetate and then wash with water (2×20 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane) to yield 21a (0.192 g, 0.79 mmol, 79%) as a brown powder.

Workup

  1. washwash with water (2×20 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed (dichloromethane)

Sources & evidence

ORD record
ord-5ad65b8ce0c9495ebce5fefd7e2fea53
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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