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

HRID 972232ノート

反応式

HRID 972232 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97738225ff26475295f1cca2de6157e9
出典データセット
uspto-grants-1977_10
特許番号
US04052407

反応ノート

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