Dimethyl Sulfoxide → HCID 68124563, compound

HRID 1730092Notes

Reaction equation

HRID 1730092 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([CH:10]=O)[CH:8]=[CH:9][C:3]=2[O:2]1.[NH:12]([CH2:19][CH2:20][C:21]#[N:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CS(C)=O.C[O-].[Na+]>CO>[NH:12]([CH:19]=[C:20]([CH2:10][C:7]1[CH:8]=[CH:9][C:3]2[O:2][CH2:1][O:5][C:4]=2[CH:6]=1)[C:21]#[N:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8438PiperonalHCID 141003-AnilinopropionitrileHCID 10942334Sodium Methoxide

Product 1

HCID 68124563HCID 68124563, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Piperonaldehyde (45 g.), β-anilinopropionitrile (52 g.) and dimethylsulfoxide (96 ml.) were heated together to 120° C and a solution of sodium methylate (2.5 g.) in methanol (12 ml.) was added over a 5 min. period. The temperature was maintained at 115°-120° C for 1 hr. and the mixture was then poured into ice-water. The resulting gum was collected by decantation and was likewise washed with water (2 × 100 ml.). Methanol (100 ml.) was then added and the mixture was heated until solution was complete. Cooling to 5° C gave β-anilino-α-piperonylacrylonitrile as a crystalline solid which was collected, and washed with cold methanol, ether, and pentane. Wt.=45 g. (54%) m.p. 150.5°-151° C (recrystallised from methanol).

Workup

  1. temperatureThe temperature was maintained at 115°-120° C for 1 hr
  2. customThe resulting gum was collected by decantation
  3. washwas likewise washed with water (2 × 100 ml.)
  4. additionMethanol (100 ml.) was then added
  5. temperaturethe mixture was heated until solution

Sources & evidence

ORD record
ord-8b339a5bab804cce89d4be3181e8bf8f
Source dataset
uspto-grants-1976_11
Patent number
US03991050

Reaction notes

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