Methanethioamide → 4-(6-Carbomethoxy hexyl)-thiazole-5-carboxylic acid methylester

HRID 972231Notes

Reaction equation

HRID 972231 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4](Cl)[C:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[CH:19]([NH2:21])=[S:20]>CO>[CH3:1][O:2][C:3]([C:4]1[S:20][CH:19]=[N:21][C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:18]

Participants

4

Reactant 2

HCID 3005587MethanethioamideHCID 545606959-Carbomethoxy-2-chloro-3ketononanic acid methylester

Product 1

HCID 538158814-(6-Carbomethoxy hexyl)-thiazole-5-carboxylic acid methylester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.8 g of 9-carbomethoxy-2-chloro-3ketonononoic acid methylester (VI) and 4.5 of thioformamide (VII, R1 = H) were refluxed in 90 ml of methanol for 1 hour, then methanol was evaporated in vacuo, and the distillation residue was dissolved in 150 ml of 2 N hydrochloric acid. The obtained solution was neutralized with a 5 % solution of sodium carbonate, saturated with ammonium sulphate and extracted with 3 × 150 ml of diethyl ether. The ethereal extract was dried over sodium sulphate, then ether was evaporated. Thus 16 g of crude 4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid methylester (VIII, R1 = H) were obtained which could be used without any further purification for the preparation of 4-(6-carboxyhexyl)-thiazole-5-carboxylic acid (IX, R1 = H) according to point (e).

Workup

  1. custommethanol was evaporated in vacuo
  2. dissolutionthe distillation residue was dissolved in 150 ml of 2 N hydrochloric acid
  3. extractionextracted with 3 × 150 ml of diethyl ether
  4. extractionThe ethereal extract
  5. dry with materialwas dried over sodium sulphate
  6. customether was evaporated

Sources & evidence

ORD record
ord-5902f9d9e87c4d739763be28d72e04d1
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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