Water → 2-Methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid

HRID 972235ノート

反応式

HRID 972235 の反応式
[CH3:1][C:2]1[S:3][C:4]([C:16]([OH:18])=[O:17])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[N:6]=1.O.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)C>CO.CCCCCC>[CH3:1][C:2]1[S:3][C:4]([C:16]([OH:18])=[O:17])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:20])=[O:14])[N:6]=1

参加物

7

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 214064232-Methyl-4-(6-carboxyhexyl)-thiazole-5-carboxylic acid

生成物 1

HCID 214064072-Methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid収率 79.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8058Hexane溶媒

実験手順

5.15 g of 2-methyl-4-(6-carboxyhexyl)-thiazole-5-carboxylic acid (IX, R1 = CH3) and 5.4 g of p-toluenesulphonic acid monohydrate were dissolved in 200 ml of methanol. The reaction mixture was stirred for 2 hours at room temperature, then poured onto 500 ml of water. After saturating the aqueous solution with ammonium sulphate it was extracted with 3 × 200 ml of ethyl acetate, the ethyl acetate extract was washed with water, dried over sodium sulphate and evaporated in vacuo. Recrystallization of the obtained crude product from a mixture of diethyl ether and n-hexane afforded 4.3 g of 2-methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid (X, R1 = CH3). M.p.: 106°-107° C. IR spectrum (KBr): ν OH (carboxylic acid) 3200-2200, ν C=O 1735, 1695, ν C-O 1235 cm-1.

後処理

  1. concentrationAfter saturating the aqueous solution with ammonium sulphate it
  2. extractionwas extracted with 3 × 200 ml of ethyl acetate
  3. extractionthe ethyl acetate extract
  4. washwas washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customRecrystallization of the
  8. customobtained crude product

出典と根拠

ORDレコード
ord-30102082f75643a0a407e1bb84ec3495
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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