Water → HCID 53911951, compound

HRID 369899Notes

Reaction equation

HRID 369899 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][C:24]=1[C:25](=[O:36])[CH:26]=[CH:27][C:28]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:29])[O:8][CH2:9][C:10]([NH:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)=[O:11])C=C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO.O1CCOCC1.[C].[Pd]>[OH:4][C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][C:24]=1[C:25](=[O:36])[CH:26]=[CH:27][C:28]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:29])[O:8][CH2:9][C:10]([NH:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)=[O:11]

Participants

7

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 54129727HCID 54129727, compound

Product 1

HCID 53911951HCID 53911951, compoundYield 23.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-{3-Allyloxy-4-[3-(1-piperidinyl)carbonylacryloyl]phenoxymethylcarbonylamino}benzothiazole (0.55 g) is dissolved in methanol (70 ml) and dioxane (40 ml), and thereto are added 10% palladium-carbon (0.15 g), p-toluenesulfonic acid monohydrate (70 mg) and water (3 ml). The mixture is subjected to deaeration, and the mixture is refluxed under nitrogen atmosphere overnight. The mixture is filtered through a cerite pad, and to the filtrate is added water-methylene chloride, and the mixture is separated, and dried over sodium sulfate. The residue is crystallized from ethanol-methylene chloride, and recrystallized from dimethylformamide-ethanol to give 2-{3-hydroxy-4-[3-(1-piperidinyl)carbonylacryloyl]phenoxymethylcarbonylamino}benzothiazole (120 mg).

Workup

  1. temperaturethe mixture is refluxed under nitrogen atmosphere overnight
  2. filtrationThe mixture is filtered through a cerite pad
  3. additionto the filtrate is added water-methylene chloride
  4. customthe mixture is separated
  5. dry with materialdried over sodium sulfate
  6. customThe residue is crystallized from ethanol-methylene chloride
  7. customrecrystallized from dimethylformamide-ethanol

Sources & evidence

ORD record
ord-b6f01b80dec144fc9286aa9d2437c931
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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