Water → 4-(6-Carbomethoxyhexyl)-thiazole-5-carboxylic acid

HRID 972233Notes

Reaction equation

HRID 972233 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][S:13][C:14]=1[C:15]([OH:17])=[O:16])([OH:3])=[O:2].O.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)C>CO.CCCCCC>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][S:13][C:14]=1[C:15]([OH:17])=[O:16])([O:3][CH3:19])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 214064084-(6-Carboxyhexyl)-thiazole-5-carboxylic acid

Product 1

HCID 214064114-(6-Carbomethoxyhexyl)-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

9.2 g of 4-(6carboxyhexyl)-thiazole-5-carboxylic acid (IX, R1 = H) and 10.2 g of p-toluenesulphonic acid monohydrate were dissolved in 400 ml of methanol. The obtained reaction mixture was stirred for 2 hours at room temperature, then poured onto one liter of water. After saturating the aqueous solution with ammonium sulphate it was extracted with 3 × 400 ml of ethyl acetate, then 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 7.9 of 4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid (X, R1 = H). M.p.: 113°-114° C.

Workup

  1. customThe obtained reaction mixture
  2. concentrationAfter saturating the aqueous solution with ammonium sulphate it
  3. extractionwas extracted with 3 × 400 ml of ethyl acetate
  4. extractionthe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. customRecrystallization of the
  9. customobtained crude product

Sources & evidence

ORD record
ord-be8d03e7b1094f588548e72a7bc72944
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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