N-Carbethoxyphthalimide → HCID 20461678, compound

HRID 543502Notes

Reaction equation

HRID 543502 reaction equation
[F:1][CH:2]([F:9])[CH:3]([NH2:8])[CH2:4][C:5]([CH3:7])=[CH2:6].C(N1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])(OCC)=O>C1C=CC=CC=1>[F:1][CH:2]([F:9])[CH:3]([N:8]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])[CH2:4][C:5]([CH3:7])=[CH2:6]

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 13116879HCID 13116879, compound

Product 1

HCID 20461678HCID 20461678, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of crude 1.1-difluoro-2-amino-4-methyl-4-pentene (20 g, evaluated 110 mmoles) prepared as in Step A above, N-carbethoxyphthalimide (24 g, 110 mmoles) in benzene (300 mL) is kept overnight at room temperature. The solution is concentrated under vacuum, the oily residue is dissolved in methylene chloride (400 mL) and treated with 8 g of triethylamine during one night at room temperature. The solution is extracted with water, twice with 1 N hydrochloric acid and twice with water again. Evaporation of the organic layer affords an oily residue which is crystallized from petroleum ether at -5° C. (19.2 g, yield based on methallyl chloride: 45%).

Workup

  1. concentrationThe solution is concentrated under vacuum
  2. dissolutionthe oily residue is dissolved in methylene chloride (400 mL)
  3. additiontreated with 8 g of triethylamine during one night at room temperature
  4. extractionThe solution is extracted with water, twice with 1 N hydrochloric acid and twice with water again
  5. customEvaporation of the organic layer
  6. customaffords an oily residue which
  7. customis crystallized from petroleum ether at -5° C.
  8. custom(19.2 g, yield based on methallyl chloride: 45%)

Sources & evidence

ORD record
ord-1c8f306f1c484227b29860c8f0086ea2
Source dataset
uspto-grants-1984_05
Patent number
US04446151

Reaction notes

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