Isobutylamine → HCID 6063397, compound

HRID 1105609Notes

Reaction equation

HRID 1105609 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7](Cl)=[O:8].[CH2:13]([NH2:17])[CH:14]([CH3:16])[CH3:15]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([NH:17][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:8]

Participants

5

Reactant 2

HCID 6558IsobutylamineHCID 53411290HCID 53411290, compound

Product 1

HCID 6063397HCID 6063397, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

A solution of 3-chlorocinnamoyl chloride (4g) in dry toluene (75 ml) was added with stirring to a solution of isobutylamine (12 ml) in dry benzene (200 ml). The reaction mixture was allowed to stand for 24 hours. The solvent was evaporated under reduced pressure and the residue thoroughly triturated with water, washed with dilute hydrochloric acid and then with water. The resulting crude product was recrystallized from ethanol-water (1:10) to give trans 3-chloro-N-isobutylcinnamamide (3.9 g), m.p. 111.5°-112.5° C. Elemental analysis, nmr and ir data were all consistent with the assigned structure. TLC gave one spot run on silica gel with 5:1 and 3:1 hexane:ethanol.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue thoroughly triturated with water
  3. washwashed with dilute hydrochloric acid
  4. customThe resulting crude product was recrystallized from ethanol-water (1:10)

Sources & evidence

ORD record
ord-6f6d42356948478f89c94a92a4dca5d6
Source dataset
uspto-grants-1982_01
Patent number
US04309444

Reaction notes

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