Dimethyl Sulfoxide → 1-[Bis(4-chlorophenyl)methyl]azetidin-3-one
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:19]2[CH2:22][CH:21]([OH:23])[CH2:20]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.CCOCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:19]2[CH2:20][C:21](=[O:23])[CH2:22]2)=[CH:14][CH:13]=1Participants
7
Procedure
To a solution of 6.3 mL (71.42 mmol) of oxalyl chloride in 250 mL of methylene chloride was added slowly 10.15 mL (142.84 mmol) of DMSO at −78° C. and stirred for 20 minutes. To this was added a solution of 11 g (35.7 mmol) of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ol in 30 mL of methylene chloride and the mixture was stirred for 30 minutes at −78° C. Then 24:7 mL (178.56 mmol) of triethylamine was added at −78° C. and the mixture was stirred for 1 h at −78° C. before warming to rt. The solution was poured into 500 mL of ether and washed with 50 mL of aq NaHCO3. The organic layer was dried over Na2SO4 and concentrated to afford the title compound.
Workup
- stirringthe mixture was stirred for 30 minutes at −78° C
- stirringthe mixture was stirred for 1 h at −78° C.
- washwashed with 50 mL of aq NaHCO3
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cdbe8d70fe6f494dbb724a87e28dd213
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906503B2
Reaction notes
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