Ethanol → HCID 67154572, compound

HRID 82986Notes

Reaction equation

HRID 82986 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]=[CH:30][C:31]=2[CH3:32])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[CH3:32][C:31]1[CH:30]=[CH:29][S:28][C:27]=1[CH2:26][O:25][CH:23]1[CH2:22][NH:21][CH2:24]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 671546491-Benzhydryl-3-((3-methylthiophen-2-yl)methoxy)azetidine

Product 1

HCID 67154572HCID 67154572, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (90 μL, 0.84 mmol) was added to a solution of 1-benzhydryl-3-((3-methylthiophen-2-yl)methoxy)azetidine (290 mg, 0.83 mmol) in dichloromethane (9 mL) at 0° C. The reaction mixture was stirred 3 hours, then 30 minutes at room temperature. Ethanol (9 mL) was added and the reaction mixture was stirred at 35° C. for an additional 3 hours. After concentration to dryness, the crude was triturated in pentane to give a yellow solid (200 mg, quantitative) which was used in the next step without further purification.

Workup

  1. custom30 minutes
  2. customat room temperature
  3. stirringthe reaction mixture was stirred at 35° C. for an additional 3 hours
  4. concentrationAfter concentration to dryness
  5. customthe crude was triturated in pentane
  6. customto give a yellow solid (200 mg, quantitative) which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-a29231d35ccc43e49e990b7683ca9297
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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