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Sulfuric Acid → 6-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1H-benzotriazol-1-acetaldehyde (2.4-dinitrophenyl)hydrazone

HRID 963664
Notes
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Reaction equation

HRID 963664 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].[N+:27]([C:30]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:31]=1[NH:39][NH2:40])([O-:29])=[O:28].OS(O)(=O)=O>C(O)C.O>[N+:27]([C:30]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:31]=1[NH:39][N:40]=[CH:18][CH:17]([CH3:20])[N:14]1[C:13]2[CH:21]=[C:9]([O:8][C:6]3[CH:5]=[C:4]([F:22])[C:3]([C:23]([F:26])([F:25])[F:24])=[C:2]([Cl:1])[CH:7]=3)[CH:10]=[CH:11][C:12]=2[N:16]=[N:15]1)([O-:29])=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3772977(2,4-Dinitrophenyl)hydrazineHCID 867479486-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl) oxy]-alpha-methyl-1H-benzotriazol-1-acetaldehyde

Product 1

HCID 867527666-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-alpha-methyl-1H-benzotriazol-1-acetaldehyde (2.4-dinitrophenyl)hydrazone

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

A solution of 6-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl) oxy]-α-methyl-1H-benzotriazol-1-acetaldehyde (0.0294 mole) in ethanol is added to a solution of 2,4-dinitrophenylhydrazine (7 g, 0.035 mole) and conc. H2SO4 (35 ml, 0.63 mole) in H2O at 50° C., allowed to come to room temperature and filtered. The solid filter cake is recrystallized from aqueous acetic acid and from ethanol to afford the title compound, mp 148°-149° C., identified by elemental and NMR analyses.

Workup

  1. customto come to room temperature
  2. filtrationfiltered
  3. filtrationThe solid filter cake
  4. customis recrystallized from aqueous acetic acid and from ethanol

Sources & evidence

ORD record
ord-fab1c786a4544b2baf153d4d8f30da17
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05763615

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes