2-(2,4-Dihydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid → 2-(2,4-Dihydroxyphenyl)thiazole-4-carboxylic acid

HRID 1748990Notes

Reaction equation

HRID 1748990 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:10][CH2:11][CH:12]([C:14]([OH:16])=[O:15])[N:13]=1>O=[Mn]=O.CN(C=O)C>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1

Participants

4

Reactant 1

HCID 1357290882-(2,4-Dihydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid

Product 1

HCID 1361835012-(2,4-Dihydroxyphenyl)thiazole-4-carboxylic acidYield 47.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6228DimethylformamideSolvent

Procedure

In a DMF (5 mL) solvent, a suspension of Compound 101b (100 mg, 0.41 mmol) and MnO2 (640 mg, 6.26 mmol) was stirred at room temperature for 24 hours. After DMF was evaporated, 1 N a NaOH solution (0.5 mL) was added to the residual. The reaction mixture was filtered, washed with water, and the filtrate was acidified by using 1 N HCl to increase a pH to 2. The produced precipitate was filtered, and washed with cold water to obtain Compound 101 (46.2 mg, 43%).

Workup

  1. customAfter DMF was evaporated
  2. addition1 N a NaOH solution (0.5 mL) was added to the residual
  3. filtrationThe reaction mixture was filtered
  4. washwashed with water
  5. temperatureto increase a pH to 2
  6. filtrationThe produced precipitate was filtered
  7. washwashed with cold water

Sources & evidence

ORD record
ord-bed42509362844039adf4a1683787154
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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