Dimethylformamide → 2-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]sulfanyl)-5-nitro-1,3-thiazole

HRID 853380Notes

Reaction equation

HRID 853380 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[S:19])[CH:14]=[CH:15][NH:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:23]1[S:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][N:27]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([S:19][C:23]3[S:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][N:27]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 182112-Bromo-5-nitrothiazoleHCID 229369807-(Benzyloxy)-6-methoxy-1,4-dihydro-4-quinolinethione

Product 1

HCID 589310522-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]sulfanyl)-5-nitro-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-(Benzyloxy)-6-methoxy-1,4-dihydro-4-quinolinethione (14.8 g), 2-bromo-5-nitro-1,3-thiazole (10.4 g), potassium carbonate (10.3 g) and dimethylformamide (150 ml) were stirred together at room temperature for 50 minutes. After adding 800 ml of water to the reaction solution, the precipitated solid was filtered out and washed with ethyl acetate to obtain 13.4 g of a light ochre powder.

Workup

  1. filtrationthe precipitated solid was filtered out
  2. washwashed with ethyl acetate
  3. customto obtain 13.4 g of a light ochre powder

Sources & evidence

ORD record
ord-bf305f9d70484975b4b923791fc33af8
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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