1,3-Benzothiazole-6-carboxamide → Benzothiazole-6-carbonitrile

HRID 552835Notes

Reaction equation

HRID 552835 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]1

Participants

3

Reactant 1

HCID 432363431,3-Benzothiazole-6-carboxamide

Product 1

HCID 10607144Benzothiazole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

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

  1. concentrationThe reaction solution was concentrated
  2. additionwater was slowly added
  3. customat 0° C
  4. extractionIt was extracted with EtOAc
  5. dry with materialthe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. 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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