Ethanol → HCID 67154565, compound

HRID 634003Notes

Reaction equation

HRID 634003 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][C:27]2[S:28][CH:29]=[C:30]([Cl:32])[CH:31]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[Cl:32][C:30]1[CH:31]=[C:27]([CH2:26][O:25][CH:23]2[CH2:22][NH:21][CH2:24]2)[S:28][CH:29]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 67154660HCID 67154660, compound

Product 1

HCID 67154565HCID 67154565, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Chloroethyl chloroformate (218 μL, 2.0 mmol) was added to a solution of 1-benzhydryl-3-((4-chlorothiophen-2-yl)methoxy)-azetidine (793 mg, 1.91 mmol) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred for 1 hour at 0° C. and for an additional 1 hour at room temperature. Ethanol (10 mL) was added and the reaction mixture was stirred overnight. After concentration to dryness, the crude mixture was precipitated from a mixture dichloromethane/diethyl ether to afford the title compound as a white solid (417 mg, 77%) which was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. concentrationAfter concentration to dryness
  3. customthe crude mixture was precipitated from a mixture dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-6d4d3022f97d4423a3380ea45993b577
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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