N-Carbethoxyphthalimide → HCID 13109083, compound

HRID 543498Notes

Reaction equation

HRID 543498 reaction equation
[F:1][CH2:2][CH:3]([NH2:8])[CH2:4][C:5]([CH3:7])=[CH2:6].C(N1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])(OCC)=O>C1C=CC=CC=1>[F:1][CH2:2][CH:3]([N:8]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH2:4][C:5]([CH3:7])=[CH2:6]

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 13109082HCID 13109082, compound

Product 1

HCID 13109083HCID 13109083, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-fluoro-2-amino-4-methyl-4-pentene (52.5 g, 450 mmoles) prepared as in step A above, N-carbethoxyphthalimide (98.55 g, 450 mmoles), and benzene (600 mL) is kept overnight at room temperature. The solution is concentrated under vacuum, the oily residue is dissolved in methylene chloride (500 mL) and treated with 50 g of triethylamine during 4 hours at room temperature. After extraction with 2 N hydrochloric acid (6×500 mL), the organic layer is dried over sodium sulfate and discoloured by filtration through a layer of silica gel and another of carbon black. The oily residue obtained after concentration (110 g) is extracted several times with petroleum ether to remove some insoluble N-carbethoxyphthalimide. Evaporation of the petroleum ether affords a yellow oil (94 g) which is crystallized from pentane at low temperature (85 g, 77%).

Workup

  1. concentrationThe solution is concentrated under vacuum
  2. dissolutionthe oily residue is dissolved in methylene chloride (500 mL)
  3. additiontreated with 50 g of triethylamine during 4 hours at room temperature
  4. extractionAfter extraction with 2 N hydrochloric acid (6×500 mL)
  5. dry with materialthe organic layer is dried over sodium sulfate
  6. filtrationdiscoloured by filtration through a layer of silica gel
  7. customThe oily residue obtained
  8. concentrationafter concentration (110 g)
  9. extractionis extracted several times with petroleum ether
  10. customto remove some insoluble N-carbethoxyphthalimide
  11. customEvaporation of the petroleum ether

Sources & evidence

ORD record
ord-8aef0b3e994543658d1b0fd5da783a6e
Source dataset
uspto-grants-1984_05
Patent number
US04446151

Reaction notes

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