Phenethylamine → HCID 70480714, compound

HRID 1980220Notes

Reaction equation

HRID 1980220 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5])#[N:2].[CH2:11]([CH2:18][NH2:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH:20](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:11]([CH2:18][NH:19][CH:20]=[C:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 1001PhenethylamineHCID 6101p-Toluenesulfonic acidHCID 25918Acetic acid, cyano-, 2-methylpropyl esterHCID 31214Ethyl orthoformate

Product 1

HCID 70480714HCID 70480714, compound

Procedure

Isobutyl cyanoacetate (5.8 g), benzylmethylamine (7 ml), triethyl orthoformate (14 ml) and p-toluenesulphonic acid (5 mg) were heated under reflux for 1 hour. The cooled reaction mixture was triturated with petroleum ether (bp 40°-60° C.) and the solid filtered off. Recrystallisation from ethanol gave isobutyl 3-(benzylmethylamino)-2-cyano-2-propenoate, m.p. 105°-106° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe cooled reaction mixture
  3. customwas triturated with petroleum ether (bp 40°-60° C.)
  4. filtrationthe solid filtered off
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-25a301d9c294464cb6b544f68b16b5cc
Source dataset
uspto-grants-1985_04
Patent number
US04508659

Reaction notes

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