3-Anilinopropionitrile → HCID 68124933, compound

HRID 1605488Notes

Reaction equation

HRID 1605488 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:17]([CH2:24][CH2:25][C:26]#[N:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C[O-].[Na+]>CS(C)=O>[NH:17]([CH:24]=[C:25]([CH2:13][C:12]1[CH:15]=[CH:16][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)[C:26]#[N:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 10942334Sodium Methoxide

Product 1

HCID 68124933HCID 68124933, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

p-Benzyloxybenzaldehyde (25g.), β-anilinopropionitrile (22 g.), and dimethylsulphoxide (25 ml.) were heated together to 95°C, and a slurry of sodium methoxide (1 g.) in dimethylsulphoxide (20 ml.) was carefully added such that the temperature rose to 105°C. The mixture was heated to 125°-130° and held at that temperature for 11/2 hr. The reaction mixture was pour into ice-water (500 ml.), and the resulting solid was collected and washed by decantation. The crude product was slurried in cold ethanol to give β-anilino-α-(p-benzyloxybenzyl) acrylonitrile. Wt. = 27g.

Workup

  1. customrose to 105°C
  2. temperatureThe mixture was heated to 125°-130°
  3. custom2 hr
  4. customthe resulting solid was collected
  5. washwashed by decantation

Sources & evidence

ORD record
ord-55773858c42f4fcf80b736282530118e
Source dataset
uspto-grants-1976_04
Patent number
US03950378

Reaction notes

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