Benzaldehyde → 2-(Benzylamino)-4,5-dimethylthiophene-3-carbonitrile

HRID 44355

Reaction equation

HRID 44355 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([BH3-])#N>C(O)(=O)C.ClC(Cl)C>[CH2:11]([NH:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrileHCID 498716Cyano-borohydride2×

Product 1

HCID 3194512-(Benzylamino)-4,5-dimethylthiophene-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (151 mg, 1.0 mmol) and benzaldehyde (106 mg, 1 mmol) in 15 mL of 4% acetic acid in dichloroethane was added silica supported cyanoborohydride (2.0 g. 2.0 mmol). The reaction was placed in a microwave reactor for 5 minutes at 135° C. Silica supported cyanoborohydride was removed by filtration, and the product was purified by prep HPLC using acetonitrile/water as solvent. MS 243 (MH+).

Workup

  1. customwas removed by filtration
  2. customthe product was purified by prep HPLC

Sources & evidence

ORD record
ord-77eaccefdd3b4e7e9282a9c89df827f7
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Linked notes

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