Formaldehyde → 3-(3,5-Difluoro-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH2:2]1.NC1C=CC=CC=1S.C=O.C(N(C(C)C)CC)(C)C.[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([F:41])[C:38]=1[O:39][CH3:40])[C:33](Cl)=[O:34]>ClCCl>[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([F:41])[C:38]=1[O:39][CH3:40])[C:33]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:34]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (316 mg) and 37% formalin (0.21 mL) in the same manner as in Example 1 was dissolved in dichloromethane (3 mL), and diisopropylethylamine (0.56 mL) and 3,5-difluoro-4-methoxybenzoyl chloride (347 mg) were added to the solution, and then the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was used for the synthesis of (c).
Workup
- distillationThe solvent was distilled off under reduced pressure and water
- additionwas added
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe obtained residue was used for the synthesis of (c)
Sources & evidence
- ORD record
- ord-a27f23469c86497395b4ff7e7ae02db8
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367843B2
Reaction notes
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