1-Chloroethyl chloroformate → HCID 18960915, compound

HRID 1708117Notes

Reaction equation

HRID 1708117 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-53a78986dea24da0a447f201d4d94c78
Source dataset
uspto-grants-1994_10
Patent number
US05356912

Reaction notes

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