Water → HCID 67936950, compound

HRID 280703Notes

Reaction equation

HRID 280703 reaction equation
[NH:1]([CH2:8][CH2:9][C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH:25]=O)=[CH:17]1.O>CS(C)=O>[NH:1]([CH:8]=[C:9]([CH2:25][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([CH3:15])[CH:17]=1)[C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 141003-AnilinopropionitrileHCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 67936950HCID 67936950, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution under nitrogen of 6.5 g (0.044 mole) of 3-anilinopropionitrile in 20 mL of dimethylsulfoxide was added 2.4 g (0.044 mole) of sodium methoxide. After stirring for 5 min, 6.5 g (0.41 mole) of 1-methylindole-3-carboxaldehyde. (E. Wenkert, J. H. Udelhofen and N. K. Bhattacharya, J. Am. Chem. Soc., 1959, 81, 3763) was added to the mixture which was then heated at 135° for 30 min, followed by cooling and dilution with 200 mL of water. The resulting solid was collected, resuspended in 150 mL of water and collected again giving 9.14 g (78%) of the title compound; the structure was confirmed by 1H-NMR.

Workup

  1. addition(E. Wenkert, J. H. Udelhofen and N. K. Bhattacharya, J. Am. Chem. Soc., 1959, 81, 3763) was added to the mixture which
  2. temperaturewas then heated at 135° for 30 min
  3. temperatureby cooling
  4. customThe resulting solid was collected
  5. customcollected again

Sources & evidence

ORD record
ord-5eec9f9c7d374f8d8abfbeceb9e07e2e
Source dataset
uspto-grants-1986_05
Patent number
US04590271

Reaction notes

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