Dimethyl Sulfoxide → HCID 54237436, compound
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][N:12]([C:14]1[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[C:16]([Cl:22])[CH:15]=1)[CH3:13].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:13][N:12]([C:14]1[CH:19]=[C:18]([CH:20]=[O:21])[CH:17]=[C:16]([Cl:22])[CH:15]=1)[CH3:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of DMSO (7.58 g, 97.0 mmol) in CH2Cl2 (100 μL) at −78° C. was added oxalyl chloride (6.16 g, 48.5 mmol) over the course of 10 min. After an additional 15 min at −78° C., a solution of 3-chloro-5-N,N-dimethylaminobenzyl alcohol (8.18 g, 44.1 mmol; see step (i) above) in CH2Cl2 (100 mL) was added over the course of 15 min. The resulting solution was stirred at −78° C. for 1 h prior to the addition of DIPEA (28.5 g, 220.5 mmol). The solution was warmed to 25° C. and stirred for 18 h, before being concentrated in vacuo to give the crude product. Flash chromatography on silica gel, eluting with Hex:EtOAc (5:1), gave 7.50 g (93%) of the sub-title compound as a yellow solid.
Workup
- temperatureThe solution was warmed to 25° C.
- stirringstirred for 18 h
- concentrationbefore being concentrated in vacuo
- customto give the crude product
- washFlash chromatography on silica gel, eluting with Hex
Sources & evidence
- ORD record
- ord-83f2b45c835d4e2f8b8f6aaf7d0732c8
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06599894B1
Reaction notes
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