Sulfuric Acid → 4-(6-Carboxyhexyl)-thiazole-5-carboxylic acid

HRID 972232Notes

Reaction equation

HRID 972232 reaction equation
C[O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[O:4].[OH-].[Na+].S(=O)(=O)(O)O>C(O)C>[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:6]1[N:7]=[CH:8][S:9][C:5]=1[C:3]([OH:4])=[O:2])([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 538158814-(6-Carbomethoxy hexyl)-thiazole-5-carboxylic acid methylester

Product 1

HCID 214064084-(6-Carboxyhexyl)-thiazole-5-carboxylic acidYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 16 g of crude 4-(6carbomethoxyhexyl)-thiazole-5-carboxylic acid methylester (VIII, R1 = H) in 50 ml of ethanol 100 ml of 2 N sodium hydroxide solution was added, the reaction mixture was refluxed for 30 minutes, then acidified with 5 N sulphuric acid under ice-cooling. On extracting the aqueous reaction mixture with 3 × 150 of ml ethyl acetate, the extract was dried over sodium sulphate and evaporated in vacuo. Recrystallization of the obtained crude product from diethylether afforded 9.4 g of 4-(6-carboxyhexyl)-thiazole-5carboxylic acid (IX, R1 = H). M.p.: 151°-153° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 30 minutes
  2. temperaturecooling
  3. extractionOn extracting the aqueous reaction mixture with 3 × 150 of ml ethyl acetate
  4. dry with materialthe extract was dried over sodium sulphate
  5. customevaporated in vacuo
  6. customRecrystallization of the
  7. customobtained crude product from diethylether

Sources & evidence

ORD record
ord-97738225ff26475295f1cca2de6157e9
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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