1,3-Benzothiazole-6-carboxamide → Benzothiazole-6-carbonitrile
Reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([NH2:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1>O=P(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[C:7]([C:10]#[N:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1,3-benzothiazole-6-carboxamide (1.96 g) in POCl3 (10 ml) was refluxed for 4 hours. The reaction solution was concentrated, and water was slowly added thereto at 0° C. It was extracted with EtOAc, and the organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20 to 60:40) to obtain 1,3-benzothiazole-6-carbonitrile as a pale yellow solid.
Workup
- concentrationThe reaction solution was concentrated
- additionwater was slowly added
- customat 0° C
- extractionIt was extracted with EtOAc
- dry with materialthe organic layer was dried over anhydrous MgSO4
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20 to 60:40)
Sources & evidence
- ORD record
- ord-241cd22099eb4a6b867cd58491a17d1e
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951825B2
Reaction notes
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