1-Chloroethyl chloroformate → HCID 18321195, compound

HRID 1782701Notes

Reaction equation

HRID 1782701 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH:13]1[CH2:18][CH2:17][N:16](CC3C=CC=CC=3)[CH2:15][CH2:14]1)[C:6](=[O:12])[NH:7]2.C(Cl)(=O)OC(Cl)C>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][N:5]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:6](=[O:12])[NH:7]2

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 18321017HCID 18321017, compound

Product 1

HCID 18321195HCID 18321195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

An ice-cold solution of 6.3 g (0.0177 mol) of 5-chloro-3,4-dihydro-3-[1-(phenylmethyl)-4-piperidinyl]-2(1H)-quinazolinone (prepared analogously to Example A4e)) in 50 ml of dichloromethane was mixed dropwise with 3.34 g (0.0234 mol) of (α-chloroethyl chlorocarbonate whilst maintaining a reaction temperature of 0° C., after which the mixture was allowed to come back slowly to room temperature. The reaction mixture was evaporated down in vacuo, the residue was taken up in 50 ml of methanol and refluxed for 4 hours. After cooling, the colourless precipitate formed was suction filtered. Yield: 2.0 g (42.5% of theory).

Workup

  1. customto come back slowly to room temperature
  2. customThe reaction mixture was evaporated down in vacuo
  3. temperaturerefluxed for 4 hours
  4. temperatureAfter cooling
  5. customthe colourless precipitate formed
  6. filtrationfiltered

Sources & evidence

ORD record
ord-71b9ae1165ef4c35902a8fb64b852509
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

Loading…