1-Chloroethyl chloroformate → HCID 18960915, compound

HRID 257443Notes

Reaction equation

HRID 257443 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[C:10]4(C)[NH:16][CH:13]([CH2:14][CH:15]=3)[CH2:12][CH2:11]4)[O:6][N:5]=2)[CH2:3][CH2:2]1.[Cl:18]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:18].[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[CH:10]4[NH:16][CH:13]([CH2:14][CH:15]=3)[CH2:12][CH2:11]4)[O:6][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 67843330HCID 67843330, compound

Product 1

HCID 18960915HCID 18960915, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-methyl-8-azabicyclo[3.2.1]oct-2-ene (525 mg, 2.3 mmol) was dissolved in dry dichlorethane (10 ml). The solution was cooled on ice and 1-chloroethyl chloroformate (370 μl, 3.4 mmol was added). The reaction mixture was heated under reflux for 1.5 h and the solvent evaporated. Methanol (20 ml) was added and the mixture heated under reflux for further 1.5 h. The mixture was treated with charcoal, filtered and concentrated in vacuo.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1.5 h
  3. customthe solvent evaporated
  4. additionMethanol (20 ml) was added
  5. temperaturethe mixture heated
  6. temperatureunder reflux for further 1.5 h
  7. additionThe mixture was treated with charcoal
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39c1a4f284214e6da36d9149b768f685
Source dataset
uspto-grants-1993_11
Patent number
US05262427

Reaction notes

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