Water → HCID 19596969, compound

HRID 611441Notes

Reaction equation

HRID 611441 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=2[N:6]=1.[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+]>[Cl:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2](/[CH:1]=[CH:18]/[C:17]3[CH:20]=[CH:21][C:14]([N:13]([CH3:22])[CH3:12])=[CH:15][CH:16]=3)=[N:6][C:5]=2[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 74794-(Dimethylamino)BenzaldehydeHCID 138735-Chloro-2-methylbenzothiazole

Product 1

HCID 19596969HCID 19596969, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

The procedure of Cuadro, et al., Il Farmaco., 47:477-488 (1992), was followed. A suspension of 2-methyl-5-chloro-benzothiazole (3.78 g, 20.6 mmol), 4-(dimethylamino)benzaldehyde (3.04 g, 20.4 mmol), and 0.5 g of benzyltriethylammonium chloride in 30 mL of 50% aqueous sodium hydroxide solution was mechanically stirred in an ultrasonic bath at room temperature for 12 hours. Water (20 mL) was added, the mixture was cooled, filtered, and the solid was washed with water to give the title compound as a yellow solid, mp 182-184° C.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. washthe solid was washed with water

Sources & evidence

ORD record
ord-85184f63846a432892ac96f0309ba3cd
Source dataset
uspto-grants-1999_12
Patent number
US06001331

Reaction notes

Loading…