Acetic Acid → N'-(3,5-difluoro-4-formylphenylsulfonyl)-N,N-dimethylformimidamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]=[CH:13][N:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[Li+].CC([N-]C(C)C)C.CN([CH:28]=[O:29])C.CC(O)=O>C1COCC1.C(NC(C)C)(C)C.[Li]CCCC.O>[F:8][C:6]1[CH:5]=[C:4]([S:9]([N:12]=[CH:13][N:14]([CH3:16])[CH3:15])(=[O:10])=[O:11])[CH:3]=[C:2]([F:1])[C:7]=1[CH:28]=[O:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- -78 °C
Procedure
To a solution of diisopropylamine (231 mL, 1.63 mmol, 2.1 eq) in THF (1 L) was slowly added BuLi (2.5M in Hex, 653 mL, 1.63 mmol, 2.1 eq) at 0° C. The solution was cooled to −78° C., and then a solution of N′-(3,5-difluorophenylsulfonyl)-N,N-dimethylformimidamide (193 g, 777 mmol) in THF (1 L) was added dropwise to the stirred LDA solution over 1 h at −78° C. and allowed to stir another 2 h at same temperature. To the reaction mixture was added anhyd DMF (72 mL, 932 mmol, 1.2 eq) and, 30 minutes later, was added AcOH (50 mL) and water. The reaction mixture was extracted with EtOAc (500 mL×3). The combined extracts were washed with brine (1 L), dried over MgSO4 and concentrated in vacuo to give N′-(3,5-difluoro-4-formylphenylsulfonyl)-N,N-dimethylformimidamide (171 g), which was used in the next step without further purification.
Workup
- customat 0° C
- extractionThe reaction mixture was extracted with EtOAc (500 mL×3)
- washThe combined extracts were washed with brine (1 L)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ebfce5adf6ee4f9daaee6a438cd85d5d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846739B2
Reaction notes
Loading…