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

HRID 1110005Notes

Reaction equation

HRID 1110005 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-e49aa8232e354685b91e54e5d88610a5
Source dataset
uspto-grants-1994_06
Patent number
US05324711

Reaction notes

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