3,5-Dimethyl-4-hydroxybenzaldehyde → 4-{[1-[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]ethylidene]hydrazonomethyl}-2,6-dimethyl-phenol

HRID 1498945Notes

Reaction equation

HRID 1498945 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14](=[N:16][NH2:17])[CH3:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[OH:18][C:19]1[C:26]([CH3:27])=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[CH3:28]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:14](=[N:16][N:17]=[CH:23][C:22]3[CH:25]=[C:26]([CH3:27])[C:19]([OH:18])=[C:20]([CH3:28])[CH:21]=3)[CH3:15])=[C:11]([CH3:13])[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 86679351{1-[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]ethylidene}-hydrazine

Product 1

HCID 1363597504-{[1-[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]ethylidene]hydrazonomethyl}-2,6-dimethyl-phenolYield 38.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (3 ml), {1-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethylidene}-hydrazine (40 mg) prepared in the Step 30-1-2 and 4-hydroxy-3,5-dimethylbenzaldehyde (29 mg) was heated under reflux for 20 hours. After the mixture was allowed to cool, the precipitated crystal was separated by filtration to give the title compound (23 mg, 38%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. temperatureto cool
  4. customthe precipitated crystal was separated by filtration

Sources & evidence

ORD record
ord-64744351d1ce4c3598e1c382365e8794
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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