Acetic Acid → 2-[6fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide

HRID 1089881Notes

Reaction equation

HRID 1089881 reaction equation
[F:1][C:2]1[C:11]([NH:12][NH2:13])=[CH:10][C:5]2[NH:6][C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[C:14](O)(=O)[CH3:15].[OH2:18]>C(O)C>[F:1][C:2]1[C:11]([N:12]2[N+:6]([O-:18])=[C:5]3[CH2:4][CH2:3][CH2:2][CH2:14][C:15]3=[N:13]2)=[CH:10][C:5]2[NH:6][C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 147716386-Fluoro-2(3H)-benzothiazolon-5-ylhydrazine

Product 1

HCID 143288132-[6fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Fluoro-2(3H)-benzothiazolon-5-ylhydrazine (6.60 g) and 4-(2-hydroxyimino-1(6)-cyclohexen-1-yl)morpholine (6.50 g) were dissolved in ethanol (120 ml), a catalytic amount of acetic acid was added thereto, and the resulting mixture was heated under reflux for 5 hours. Water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was concentrated, a mixture of cupric sulfate pentahydrate (16.0 g), water (64 g), 15% aqueous pyridine (160 g) and tetrahydrofuran (128 ml) was added thereto, and the resulting mixture was refluxed for 5 hours. After cooling, water and ethyl acetate were added thereto. The organic layer was separated from the aqueous layer, washed with dilute hydrochloric acid, dried and concentrated. The residue was purified by silica gel column chromatography using a mixture of ethyl acetate and hexane (1:9) as an eluent to give 2-[6-fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide (0.62 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. concentrationThe extract was concentrated
  5. additiona mixture of cupric sulfate pentahydrate (16.0 g), water (64 g), 15% aqueous pyridine (160 g) and tetrahydrofuran (128 ml)
  6. additionwas added
  7. temperaturethe resulting mixture was refluxed for 5 hours
  8. temperatureAfter cooling
  9. additionwater and ethyl acetate were added
  10. customThe organic layer was separated from the aqueous layer
  11. washwashed with dilute hydrochloric acid
  12. customdried
  13. concentrationconcentrated
  14. customThe residue was purified by silica gel column chromatography
  15. additiona mixture of ethyl acetate and hexane (1:9) as an eluent

Sources & evidence

ORD record
ord-f0deef7813bb4ac7a4eb4b6adaabc8b0
Source dataset
uspto-grants-1992_01
Patent number
US05079368

Reaction notes

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