Water → HCID 54209053, compound

HRID 743121Notes

Reaction equation

HRID 743121 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH2:26][CH2:27][S:28][CH3:29])(=[O:5])[CH2:2][CH2:3][CH3:4].[OH2:30].Cl[O-].[Na+].[CH2:34](Cl)Cl>>[CH:26]([O:25][CH:10]([CH3:9])[CH3:11])([CH3:27])[CH3:34].[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH2:26][CH2:27][S:28]([CH3:29])=[O:30])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 23665760Sodium Hypochlorite2×HCID 54000291HCID 54000291, compound

Product 2

HCID 7914Diisopropyl EtherHCID 54209053HCID 54209053, compoundYield 91%

Procedure

3-butyryl-4-(2,4-dimethylphenylamino)-8-(2-methylthioethoxy)quinoline (0.34 g, 0.83 mmol) was dissolved in methylene chloride (4 ml). Water (2 ml) and sodium hypochlorite (5% in water) (1.39 ml) were added and the mixture was stirred for 2 h. Another portion of sodium hypochlorite (0.5 ml) was added and the stirring was continued for 2 h. The organic layer was dried over sodium sulfate and evaporated. Trituration with isopropyl ether gave 0.32 g (91%) of the title compound.

Workup

  1. waitthe stirring was continued for 2 h
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-7683723a2b38463ebbbcb443c86093d0
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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