Semicarbazide hydrochloride → 6-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1H-benzotriazole-1-acetaldehyde semicarbazone

HRID 2293733Notes

Reaction equation

HRID 2293733 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([CH:17]([CH3:20])[CH:18]=O)[C:13]=3[CH:21]=2)[CH:5]=[C:4]([F:22])[C:3]=1[C:23]([F:26])([F:25])[F:24].Cl.[NH2:28][NH:29][C:30]([NH2:32])=[O:31].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([CH:17]([CH3:18])[CH:20]=[N:28][NH:29][C:30]([NH2:32])=[O:31])[C:13]=3[CH:21]=2)[CH:5]=[C:4]([F:22])[C:3]=1[C:23]([F:26])([F:25])[F:24]

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 867479486-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl) oxy]-alpha-methyl-1H-benzotriazol-1-acetaldehyde

Product 1

HCID 867479476-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1H-benzotriazole-1-acetaldehyde semicarbazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]-α-methyl-1H-benzotriazole-1-acetaldehyde (0.0295 mole), semicarbazide hydrochloride (4.0 g, 0.035 mole), and sodium acetate (5.8 g, 0.071 mole) in aqueous ethanol is heated to reflux temperature, cooled and filtered. The solid filter cake is recrystallized from ethanol to give the title compound as a solid, mp 170°-171° C., identified by elemental and NMR analyses.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. temperaturecooled
  4. filtrationfiltered
  5. filtrationThe solid filter cake
  6. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-a1f76f334e8244129f5638e83708baff
Source dataset
uspto-grants-1997_11
Patent number
US05686617

Reaction notes

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