Potassium Hydroxide → HCID 80571903, compound

HRID 2222198Notes

Reaction equation

HRID 2222198 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)=[N:8][CH:7]=1)=[O:5])C.[OH-].[K+]>C1COCC1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([NH:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86056606HCID 86056606, compound

Product 1

HCID 80571903HCID 80571903, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3.9 g (12.78 mmol) 2-(3,4-Dimethoxy-phenylamino)-thiazole-5-carboxylic acid ethyl ester and 12.78 ml 5M KOH in 23.5 ml THF was heated to 55° C. for 22 h. After acidification with HCl aq. The mixture was extracted with ethyl acetate and the combined organic layers washed with water, dried with MgSO4 and evaporated to dryness. Additionally precipitaed material from the aqueous phase was filtered off and dried. 2.39 g (67%) of the title compound was obtained as beige crystals. MS (m/e): 279.0 (M−H, 100%)

Workup

  1. extractionAfter acidification with HCl aq. The mixture was extracted with ethyl acetate
  2. washthe combined organic layers washed with water
  3. dry with materialdried with MgSO4
  4. customevaporated to dryness
  5. filtrationAdditionally precipitaed material from the aqueous phase was filtered off
  6. customdried

Sources & evidence

ORD record
ord-1d7c8eaa0b2045aaab8c9ff445f563df
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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