1-Chloroethyl chloroformate → HCID 19776678, compound

HRID 1612758Notes

Reaction equation

HRID 1612758 reaction equation
ClC(OC(Cl)C)=[O:3].[CH2:8]([N:15]1[CH2:20][CH2:19][O:18][CH:17]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=2)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCCl>[CH2:8]([N:15]1[CH2:20][CH2:19][O:18][CH:17]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:26][CH:27]=2)[C:16]1=[O:3])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 19776685HCID 19776685, compound

Product 1

HCID 19776678HCID 19776678, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Chloroethyl chloroformate (2.98 ml, 27.7 mmol) was added in a steady stream to a stirred solution of the N-benzyl-2-(4-tert-butylphenylmethyl)morpholine (8.94 g, 27.7 mmol) obtained in (ii) in 1,2-dichloroethane (100 ml) at 0° C. The reaction was stirred for 20 minutes and then heated under reflux for 135 minutes before cooling and evaporation in vacuo. Methanol (100 ml) was then added and the reaction heated under reflux for 1 hour before cooling, evaporation in vacuo and dissolution in chloroform (about 200 ml). This solution was washed with saturated aqueous sodium hydrogen carbonate (20 ml), dried with sodium sulphate and evaporated in vacuo. The resulting gummy solid was recrystallised from chloroform/diethyl ether to afford the desired product as a white solid, 1.5 g, M.pt. 190°-193° C., M+ --HCl found: 233.

Sources & evidence

ORD record
ord-c89134811c7d4011b07d66f10308db0c
Source dataset
uspto-grants-1993_03
Patent number
US05190958

Reaction notes

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