Acetic Acid → HCID 68123394, compound

HRID 460790Notes

Reaction equation

HRID 460790 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-:2].C(N(CC)CC)C.[O:15]=[CH:16][C:17]([Cl:20])([Cl:19])[Cl:18].C(O)(=O)C>C1C=CC=CC=1>[CH3:7][O:6][C:4]([C@H:3]1[C@H:16]([C:17]([Cl:20])([Cl:19])[Cl:18])[O:15][CH:2]=[N:1]1)=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6407ChloralHCID 8471TriethylamineHCID 547815Methyl isocyanoacetate

Product 1

HCID 68123394HCID 68123394, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.0 g of methyl α-isocyanoacetate and 5.0 g of triethylamine are dissolved in 40 ml of benzene. 7.4 g of chloral are added to the solution at 0° C under stirring. The mixture is stirred at room temperature for 4 hours. Then, the mixture is neutralized with acetic acid, and evaporated under reduced pressure to remove solvent. The residue is dissolved in 50 ml of ethyl acetate. The solution is washed with water, dried, and then evaporated under reduced pressure to remove ethyl acetate. The residue thus obtained is distilled under reduced pressure. 10.6 g of trans-4-methoxycarbonyl-5-trichloromethyl-2-oxazoline are obtained. Yield: 85% B.p. 95° C/1 mmHg

Workup

  1. stirringThe mixture is stirred at room temperature for 4 hours
  2. customevaporated under reduced pressure
  3. customto remove solvent
  4. dissolutionThe residue is dissolved in 50 ml of ethyl acetate
  5. washThe solution is washed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customto remove ethyl acetate
  9. customThe residue thus obtained
  10. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-a2a59625655d436ba411fb4f7bcf552c
Source dataset
uspto-grants-1977_12
Patent number
US04061650

Reaction notes

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