Benzoyl chloride → HCID 18707301, compound

HRID 1421954Notes

Reaction equation

HRID 1421954 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH2:21][CH2:20][CH2:19]4)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]([C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:21][CH2:20][CH2:19]4)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 18707162HCID 18707162, compound

Product 1

HCID 18707301HCID 18707301, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml of pyridine was dissolved 1 g of 2-(3,4-dimethoxyphenyl)-4-(1,2,3,4-tetrahydroquinolin-6-yl)thiazole. Thereto was added 0.44 g of benzoyl chloride at 0° C., and the mixture was stirred for 5 hours. The solution was concentrated and mixed with ethanol and water in this order. The resulting crystals were collected by filtration and recrystallized from ethanol to obtain 0.7 g of 2-(3,4-dimethoxyphenyl)-4-(1-benzoyl-1,2,3,4-tetrahydroquinolin-6-yl)thiazole as a light yellow powder.

Workup

  1. concentrationThe solution was concentrated
  2. additionmixed with ethanol and water in this order
  3. filtrationThe resulting crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d46bab10d279453c9551a171068e1934
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

Loading…