Hydrochloric Acid → HCID 68662198, compound
Reaction equation
[F:1][CH:2]([F:22])[O:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][NH:9][S:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[C:23](OCC)(=[O:27])[C:24]([O-])=[O:25].CC(C)([O-])C.[K+].Cl>C1COCC1>[F:22][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:24](=[O:25])[C:23]([OH:27])=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:10]2(=[O:12])=[O:11])=[CH:20][CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
N-[4-(Difluoromethoxy)benzyl]-1-phenylmethanesulfonamide (0.6 g, 1.83 mmol) and ethyl oxalate (0.32 g, 2.20 mmol) were mixed in THF (4 mL, dry). Under an atmosphere of nitrogen, potassium tert-butoxide (0.27 g, 2.38 mmol) was added and the reaction mixture was heated in a microwave reactor at 150° C. for 10 mins and then at 150° C. for 5 mins. The mixture was then cooled in an ice-bath and HCl (10%, 1 mL) was added, pH˜1. The mixture was evaporated to remove THF and the residue was extracted with DCM (20 mL). The extract was dried (MgSO4) and evaporated to give the crude product (0.634 g). It was used in the next step without further purification.
Workup
- temperatureThe mixture was then cooled in an ice-bath
- customThe mixture was evaporated
- customto remove THF
- extractionthe residue was extracted with DCM (20 mL)
- dry with materialThe extract was dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-745268b0a7df45b0a239785518ccb393
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582629B2
Reaction notes
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