Benzaldehyde → HCID 98475, compound

HRID 1638769Notes

Reaction equation

HRID 1638769 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].C1(C)C=CC=CC=1>O>[CH:1]([C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 1140TolueneHCID 84462-MethylbenzothiazoleHCID 14798Sodium Hydroxide

Product 1

HCID 98475HCID 98475, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methylbenzothiazole (1.49 g, 0.01 mol), benzaldehyde (1.27 g, 0.012 mol), 50% sodium hydroxide solution (3 ml), toluene (5 ml) and compound 1 (1 mmol) was stirred at reflux temperature for 4 hours. The reaction mixture was allowed to cool to room temperature and then diluted with water (10 ml). The organic layer was separated and the aqueous phase extracted with toluene. The combined organic portions were dried over magnesium sulphate and evaporated to give a solid residue which was crystallized from ethanol to give the corresponding 2-styrylbenzothiazole.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous phase extracted with toluene
  4. dry with materialThe combined organic portions were dried over magnesium sulphate
  5. customevaporated
  6. customto give a solid residue which
  7. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-fc75a13287004160b16b2cb793cb40c0
Source dataset
uspto-grants-1989_11
Patent number
US04880894

Reaction notes

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