Formaldehyde → 3-(3-Cyano-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:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:25](Cl)=[O:26])#[N:21]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:25]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:26])#[N:21]Participants
7
Procedure
2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (1.89 g) and 37% formalin (1.25 mL) in the same manner as in Example 1 was dissolved in chloroform (20 mL), and triethylamine (2.08 mL) and 3-cyano-4-methoxybenzoyl chloride were added to the solution, and then the mixture was stirred at room temperature for 2 hours. The organic solvent was distilled off under reduced pressure and 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 (e).
Workup
- distillationThe organic solvent was distilled off under reduced pressure
- extractionextracted 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 (e)
Sources & evidence
- ORD record
- ord-54f295efec0b4b65a99d0b418848b883
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367843B2
Reaction notes
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