Borane;tetrahydrofuran → HCID 22730134, compound
Reaction equation
[F:1][C:2]([F:13])([S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([NH2:5])=O.B.C1COCC1>C1COCC1>[F:13][C:2]([F:1])([S:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:3][NH2:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2,2-difluoro-2-phenylsulfanylacetamide (1 g, 4.92 mmol) in THF at room temperature was treated with BH3.THF (1M, 25 mL), stirred for 18 hours, quenched with methanol (5 mL), and concentrated. The concentrate was treated with 2M HCl and heated to 80° C. for 30 minutes and concentrated. The concentrate was partitioned between dichloromethane and saturated sodium bicarbonate, and the organic phase was dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 190 (M+H)+.
Workup
- customquenched with methanol (5 mL)
- concentrationconcentrated
- additionThe concentrate was treated with 2M HCl
- concentrationconcentrated
- customThe concentrate was partitioned between dichloromethane and saturated sodium bicarbonate
- dry with materialthe organic phase was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e8691be5ebeb4ee99d4d2737c72a231f
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06720338B2
Reaction notes
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