Ethanol → 3-(Thiophen-2-ylthio)-azetidine hydrochloride
Reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([S:25][C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClC(Cl)C>[ClH:1].[S:27]1[CH:28]=[CH:29][CH:30]=[C:26]1[S:25][CH:23]1[CH2:24][NH:21][CH2:22]1Participants
5
Conditions
- Temperature
- 70 °C
Procedure
1-Chloroethyl chloroformate (140 μL, 1.3 mmol) was added to a solution of 1-benzhydryl-3-(thiophen-2-ylthio)-azetidine (340 mg, 1.00 mmol) in dichloroethane (11 mL) at 0° C. The reaction mixture was stirred for 3 hours at room temperature and for 2 hours at 70° C. Ethanol (11 mL) was added and the reaction mixture was stirred for an additional 2 days at room temperature. After concentration to dryness, the residue was triturated in pentane (2×20 mL) to afford a brown oil (171 mg, 81%) which was used in the next step without further purification.
Workup
- stirringthe reaction mixture was stirred for an additional 2 days at room temperature
- concentrationAfter concentration to dryness
- customthe residue was triturated in pentane (2×20 mL)
Sources & evidence
- ORD record
- ord-8ce950bea410438d9f7cbf9215c0d58c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846711B2
Reaction notes
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