Butylamine → HCID 57200515, compound

HRID 231462Notes

Reaction equation

HRID 231462 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[C:10]([C:14]#[N:15])[C:11]([OH:13])=O)[CH:3]=1.S(Cl)(Cl)=O.[CH2:20]([NH2:24])[CH2:21][CH2:22][CH3:23]>Cl>[CH2:20]([NH:24][C:11](=[O:13])[C:10](=[C:4]1[CH2:5][C:6]([CH3:8])([CH3:9])[CH2:7][C:2]([CH3:1])=[CH:3]1)[C:14]#[N:15])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 24386Thionyl ChlorideHCID 54572540HCID 54572540, compound

Product 1

HCID 57200515HCID 57200515, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2(3,5,5-trimethyl-2-cyclohexenylidene) cyanoacetic acid (0.2 mol) and thionyl chloride (50 mls) were refluxed together for 1 hr. The acid chloride was then added dropwise with stirring to n-butylamine (0.4 mol) in petroleum ether (340 mls). The flask may have to be cooled with an ice bath. After addition, 1N HCl (150 mls) was added and the mixture stirred. The mixture was allowed to separate and the upper layer was washed until acid free. It was then treated with 1.4 g activated carbon, then n-butyl (3,5,5-trimethyl-2-cyclohexenylidene) cyanoacetamide was isolated. Ref. J. Am. Chem. Soc., 1949, 71, 2215.

Workup

  1. temperatureto be cooled with an ice bath
  2. additionwas added
  3. customto separate
  4. washthe upper layer was washed until acid free
  5. additionIt was then treated with 1.4 g

Sources & evidence

ORD record
ord-682cec010c324baeba3700821b9fb90c
Source dataset
uspto-grants-1989_07
Patent number
US04847073

Reaction notes

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