Pyridine → HCID 13556609, compound

HRID 649644Notes

Reaction equation

HRID 649644 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[N:16][OH:17])=[CH:4][CH:3]=1.N1C=CC=CC=1.O1CCCC1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[N+:16]([O-:17])=[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]3=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 136393668HCID 136393668, compound

Product 1

HCID 13556609HCID 13556609, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 2-(4-chlorophenylhydrazono)-cyclohexanone oxime (1.6 g) in a mixture of 15% aqueous solution of pyridine (25 ml) and tetrahydrofuran (20 ml), a solution of cupric sulfate (CuSO4.5H2O) (2.5 g) in water (10 ml) was added at room temperature, and the resultant mixture was heated under reflux for 2 hours. After cooling, water was added to the mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated aqueous cupric sulfate solution and water in order, dried and concentrated. The residue was purified by silica gel column chromatography using a mixture of n-hexane and ethyl acetate as an eluent to give 0.2 g of 2-(4-chlorophenyl)-4,5,6,7-tetrahydro-1,2,3-benzotriazol-1-oxide (Compound No. 1). M.P., 100°-101° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. extractionwas then extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous cupric sulfate solution and water in order
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. additiona mixture of n-hexane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-bba87b5af665495a8c616dd90caa2779
Source dataset
uspto-grants-1988_04
Patent number
US04740619

Reaction notes

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