Thioanisole → 6-Methoxy-4-[(5-nitro-1,3-thiazol-2-yl)sulfanyl]-7-quinolinol

HRID 853381Notes

Reaction equation

HRID 853381 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([S:19][C:20]3[S:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][N:24]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:29][O:28][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[S:19][C:20]1[S:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][N:24]=1

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 589310522-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]sulfanyl)-5-nitro-1,3-thiazole

Product 1

HCID 1359899416-Methoxy-4-[(5-nitro-1,3-thiazol-2-yl)sulfanyl]-7-quinolinolYield 88.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]sulfanyl}-5-nitro-1,3-thiazole (2.0 g), trifluoroacetic acid (20 ml) and thioanisole (2 ml) were stirred together at 65° C. for 90 minutes. The mixture was returned to room temperature, the solvent was distilled off under reduced pressure, 40 ml of methanol was added to the residue, and then sodium bicarnobate water was added until the foaming subsided. The precipitated solid was filtered out to obtain 1.4 g of a yellow powder.

Workup

  1. customwas returned to room temperature
  2. distillationthe solvent was distilled off under reduced pressure, 40 ml of methanol
  3. additionwas added to the residue
  4. additionsodium bicarnobate water was added until the foaming
  5. filtrationThe precipitated solid was filtered out

Sources & evidence

ORD record
ord-d28b8315ccb54fb992c9eec40b7f404c
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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