1-Chloroethyl chloroformate → HCID 67925064, compound

HRID 344692Notes

Reaction equation

HRID 344692 reaction equation
C[N:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)[CH2:3]1.[Cl:13]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:13].[O:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:4]1[CH2:3][NH:2][CH2:7][CH2:6][CH:5]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 54089363HCID 54089363, compound

Product 1

HCID 67925064HCID 67925064, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4 g of 1-methyl-3-(oxazol-2-yl)-1,2,5,6-tetrahydropyridine in 80 cm3 of dichloroethane is cooled to -5° C. under inert atmosphere and 3.88 g of alpha-chloroethyl chloroformate is added. The mixture is heated under reflux for one hour 30 minutes, evaporated, the residue is taken up in diethylether, followed by filtering. The ethereal phase is concentrated, the residue is taken up in 30 cm3 of methanol, heated at boiling point for 40 minutes and evaporated to dryness. After crystallization from ethanol and ether, 2.1 g of expected product is obtained. M.p.=188°-191° C.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for one hour 30 minutes
  4. customevaporated
  5. filtrationby filtering
  6. concentrationThe ethereal phase is concentrated
  7. temperatureheated
  8. customfor 40 minutes
  9. customevaporated to dryness
  10. customAfter crystallization from ethanol and ether

Sources & evidence

ORD record
ord-c3999ac39aff44b39e3417f323a8222e
Source dataset
uspto-grants-1991_10
Patent number
US05053416

Reaction notes

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