Methanol → HCID 15718365, compound

HRID 1199702Notes

Reaction equation

HRID 1199702 reaction equation
O1CCOCC1.CO.[CH3:9][O:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19](/[CH:21]=[CH:22]/[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=3)=[N:18][C:17]=2[CH:32]=1)=[O:12].[Cl-].[Ca+2].[Cl-]>O.[Zn]>[NH2:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)/[CH:22]=[CH:21]/[C:19]1[S:20][C:16]2[CH:15]=[CH:14][C:13]([C:11]([O:10][CH3:9])=[O:12])=[CH:32][C:17]=2[N:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 312751,4-DioxaneHCID 5284359Calcium ChlorideHCID 17885020HCID 17885020, compound

Product 1

HCID 15718365HCID 15718365, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To a solvent mixture of 50 ml of dioxane and 30 ml of methanol, 2.0 g of 5-methoxycarbonyl-2-(trans-3-nitrostyryl)benzothiazole was added and, under vigorous stirring, a solution of 0.37 g of calcium chloride in 55 ml of water and 9.8 g of zinc powder were added, followed by refluxing for 2 hours. After cooled to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure, and the solid residue formed was washed with toluene to give 1.4 g (yield 77%) of the title compound.

Workup

  1. additionwas added and, under vigorous stirring
  2. temperatureby refluxing for 2 hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe solid residue formed
  6. washwas washed with toluene

Sources & evidence

ORD record
ord-be8055b0b8774106ac52d167a1ee3968
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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