Dimethyl Sulfoxide → HCID 59457459, compound
Reaction equation
C[N+]([O-:5])(C)C.ClCCl.CS(C)=O.Cl[CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][Cl:30])=[CH:22][CH:21]=2)[O:18][CH:19]=1>O>[Cl:30][CH2:29][CH2:28][CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[O:18][CH:19]=[C:15]([CH:14]=[O:5])[N:16]=2)=[CH:21][CH:22]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A cold (−20° C.) solution of anhydrous trimethylamine N-oxide (2.10 g, 27.96 mmol) in a dry mixture of dichloromethane and dimethylsulfoxide (20 ml, 1/3 v/v) is treated with a solution of 4-chloromethyl-2-[4-(3-chloro-propoxy)-phenyl]-oxazole ax57 (2.00 g, 6.99 mmol) in the same mixture of solvents (20 ml). The mixture is then allowed to warm up to 20° C. and is stirred at that temperature for 24 h. The dark mixture is then poured into water (50 ml) and extracted with dichloromethane. The organic phases are concentrated and the resulting DMSO solution is treated with ether and water. The heterogeneous mixture is further extracted with ether (2×20 ml). The organic phases are then dried over magnesium sulfate and concentrated to afford 760 mg of 2-[4-(3-chloro-propoxy)-phenyl]-oxazole-4-carbaldehyde i100.
Workup
- extractionextracted with dichloromethane
- concentrationThe organic phases are concentrated
- additionthe resulting DMSO solution is treated with ether and water
- extractionThe heterogeneous mixture is further extracted with ether (2×20 ml)
- dry with materialThe organic phases are then dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2fcc531f785c4f0685fbc1d85a92203f
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790720B2
Reaction notes
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