Thioglycolic Acid → HCID 66665769, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:32])=[C:6]([C:8]2([CH:29]([F:31])[F:30])[N:13](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[C:12](=[O:26])[C:11]([CH3:28])([CH3:27])[O:10][CH2:9]2)[CH:7]=1.C(O)(=O)CS.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:32])=[C:6]([C:8]2([CH:29]([F:31])[F:30])[NH:13][C:12](=[O:26])[C:11]([CH3:28])([CH3:27])[O:10][CH2:9]2)[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-2,2-dimethyl-4-(2-nitro-benzenesulfonyl)-morpholin-3-one (6.29 g, 11.71 mmol) and thioglycolic acid (1.83 g, 19.90 mmol) in 63 mL DMF was added potassium carbonate (6.47 g, 46.8 mmol). The reaction mixture was heated to 60° C. After 120 minutes, additional thioglycolic acid (324 mg, 3.51 mmol) was added. 30 minutes later on, the reaction mixture was cooled to room temperature and partitioned between EtOAc and water. The layers were separated, washed with saturated aqueous NaHCO3, brine and EtOAc. The combined organic layers were dried over MgSO4.H2O and evaporated. The crude product was crystallized from TBME/hexane to give 3.14 g of the title compound as white crystals.
Workup
- temperature30 minutes later on, the reaction mixture was cooled to room temperature
- custompartitioned between EtOAc and water
- customThe layers were separated
- washwashed with saturated aqueous NaHCO3, brine and EtOAc
- dry with materialThe combined organic layers were dried over MgSO4.H2O
- customevaporated
- customThe crude product was crystallized from TBME/hexane
Sources & evidence
- ORD record
- ord-cc7351af939f48c992bba0f7a71f1127
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338413B1
Reaction notes
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