Dimethyl Sulfoxide → HCID 53880571, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][N:13]=[C:14]([CH:32]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=1)[CH2:33][CH2:34][OH:35])[CH2:15][O:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:11][O:12][N:13]=[C:14]([CH:32]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=1)[CH2:33][CH:34]=[O:35])[CH2:15][O:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:21]=[C:20]([C:28]([F:29])([F:30])[F:31])[CH:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Dissolve oxalyl chloride (2.01 g, 15.82 mmol) in dry CH2Cl2 (30 mL) and cool to -78° C. under N2, add DMSO (2.47 g, 31.64 mmol) in dry CH2Cl2 (12 mL) dropwise and stir at -78° C. for 15 mins. Add the product of Step 7 (6.56 g, 12.66 mmol) in dry CH2Cl2 (20 mL) dropwise and stir at -78° C. for 3 h. Add diisopropylethylamine (4.91 g, 37.97 mmol) and stir at -78° C. for 1 h. Warm slowly to 0° C. and stir at 0° C. for 30 mins. Add water (150 mL) and extract with CH2Cl2. Wash combined organic extracts with saturated aqueous NaCl, dry (MgSO4), filter, and concentrate to give 6.53 g (12.66 mmol, 100%) of a yellow oil. MS (FAB): m/e 516 (M+1).
Workup
- stirringstir at -78° C. for 3 h
- temperatureWarm slowly to 0° C.
- stirringstir at 0° C. for 30 mins
- extractionAdd water (150 mL) and extract with CH2Cl2
- washWash
- dry with materialdry (MgSO4)
- filtrationfilter
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-5a20c3c232804f16a57ff2176ca26b7f
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840725
Reaction notes
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