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

HRID 1010245Notes

Reaction equation

HRID 1010245 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-84c71c8228ee4e3eb0a03cc5eabf62a6
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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