Acetic Acid → HCID 14328817, compound

HRID 1089880Notes

Reaction equation

HRID 1089880 reaction equation
[F:1][C:2]1[C:14]([NH:15][NH2:16])=[CH:13][C:5]2[N:6]([CH:10]([CH3:12])[CH3:11])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[OH:17][N:18]=[C:19]1[CH2:24][CH2:23][CH2:22][CH:21]=[C:20]1N1CCOCC1.C(O)(=O)C.O>C(O)C>[CH:10]([N:6]1[C:5]2[CH:13]=[C:14]([N:15]3[N+:18]([O-:17])=[C:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C:20]4=[N:16]3)[C:2]([F:1])=[CH:3][C:4]=2[S:8][C:7]1=[O:9])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14053885HCID 14053885, compoundHCID 73454462HCID 73454462, compound

Product 1

HCID 14328817HCID 14328817, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Fluoro-3-(1-methylethyl)-2(3H)-benzothiazolon-5-ylhydrazine (1.11 g) and 4-(3-hydroxyimino-1-cyclohexen-2-yl)morpholine (0.90 g) were dissolved in ethanol (20 ml), a catalytic amount of acetic acid was added thereto, and the resultant mixture was heated under reflux for 3 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was distilled under reduced pressure to remove the solvent and combined with a mixture of 15% aqueous pyridine (30 ml), tetrahydrofuran (20 ml) and cupric sulfate pentahydrate (2.2 g), followed by refluxing for 2 hours. After cooling, water and ethyl acetate were added to the reaction mixture. The organic layer was separated from the water layer, washed with dilute hydrochloric acid, dried and concentrated. The residue was crystallized from ether to give 2-[3-isopropyl-6-fluoro-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-benzotriazole-1-oxide (Compound No. 3; 0.7 g). m.p., 92.5° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionwas then extracted with ethyl acetate
  3. distillationThe extract was distilled under reduced pressure
  4. customto remove the solvent
  5. additioncombined with a mixture of 15% aqueous pyridine (30 ml), tetrahydrofuran (20 ml) and cupric sulfate pentahydrate (2.2 g)
  6. temperatureby refluxing for 2 hours
  7. temperatureAfter cooling
  8. additionwater and ethyl acetate were added to the reaction mixture
  9. customThe organic layer was separated from the water layer
  10. washwashed with dilute hydrochloric acid
  11. customdried
  12. concentrationconcentrated
  13. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-f9ccab83f60a44d2b6e21b0c91f04bc2
Source dataset
uspto-grants-1992_01
Patent number
US05079368

Reaction notes

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