Ethanol → 2-Methyl-4-(6-carboxyhexyl)-thiazole-5-carboxylic acid

HRID 972234Notes

Reaction equation

HRID 972234 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.[CH2:27](O)C>>[CH3:27][C:8]1[S:9][C:5]([C:3]([OH:2])=[O:4])=[C:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[N:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 538158814-(6-Carbomethoxy hexyl)-thiazole-5-carboxylic acid methylester

Product 1

HCID 214064232-Methyl-4-(6-carboxyhexyl)-thiazole-5-carboxylic acid

Procedure

The solution of 8 g of crude 2-methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid methylester (VIII, R1 = CH3) in 25 ml of ethanol was treated with 40 ml of 2 N sodium hydroxide solution. The reaction mixture was refluxed for 30 minutes, then acidified with 5 N sulphuric acid under ice-cooling. After extracting the aqueous reaction mixture with 3 × 75 ml of ethyl acetate, the extract was dried over sodium sulphate and evaporated in vacuo. The obtained crude product was recrystallized from a mixture of acetone and n-hexane, affording 5.3 g of 2-methyl-4-(6-carboxyhexyl)-thiazole-5-carboxylic acid (IX, R1 = CH3). M.p.: 147-149° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. temperaturecooling
  3. extractionAfter extracting the aqueous reaction mixture with 3 × 75 ml of ethyl acetate
  4. dry with materialthe extract was dried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe obtained crude product
  7. customwas recrystallized from a mixture of acetone and n-hexane

Sources & evidence

ORD record
ord-54b3328924ad4d36a0df9c9d99756888
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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