Oxalyl chloride → 2-Methyl-4-(6-carbomethoxyhexyl)-5-hydroxymethyl-thiazole

HRID 972236Notes

Reaction equation

HRID 972236 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:17](O)=[O:18])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:6]=1.C(Cl)(=O)C(Cl)=O>C1C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([CH2:17][OH:18])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:6]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 214064072-Methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid

Product 1

HCID 214064172-Methyl-4-(6-carbomethoxyhexyl)-5-hydroxymethyl-thiazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To the solution of 4.15 g of 2-methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid (X, R1 = CH3) in 50 ml of anhydrous benzene 4.2 ml of oxalyl chloride were added dropwise, and the reaction mixture was allowed to stand overnight at room temperature, then benzene and excess oxalyl chloride were evaporated in vacuo. The obtained residue containing 2-methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid chloride (XI, R1 = CH3) was dissolved in 20 ml of anhydrous dioxane, and a suspension of 1.1 g of sodium borohydride in 20 ml of anhydrous dioxane was added dropwise to the solution under continuous stirring. Stirring of the reaction mixture was continued for 30 minutes at room temperature and for further 60 minutes at 80° C. When the reaction mixture was cooled to room temperature, 25 ml of water were dropwise added under ice-cooling to the reaction mxiture, and stirring was continued for 2 hours at room temperature. Subsequently, the aqueous reaction mixture was extracted with 3 × 50 ml of ethyl acetate. The ethyl acetate extract was dried over sodium sulphate and evaporated in vacuo, yielding 2.95 of crude product.

Workup

  1. custombenzene and excess oxalyl chloride were evaporated in vacuo
  2. additionThe obtained residue containing 2-methyl-4-(6-carbomethoxyhexyl)-thiazole-5-carboxylic acid chloride (XI, R1 = CH3)
  3. dissolutionwas dissolved in 20 ml of anhydrous dioxane
  4. additiona suspension of 1.1 g of sodium borohydride in 20 ml of anhydrous dioxane
  5. additionwas added dropwise to the solution under continuous stirring
  6. waitwas continued for 30 minutes at room temperature and for further 60 minutes at 80° C
  7. addition25 ml of water were dropwise added under ice-
  8. temperaturecooling to the reaction mxiture
  9. stirringstirring
  10. waitwas continued for 2 hours at room temperature
  11. extractionSubsequently, the aqueous reaction mixture was extracted with 3 × 50 ml of ethyl acetate
  12. extractionThe ethyl acetate extract
  13. dry with materialwas dried over sodium sulphate
  14. customevaporated in vacuo
  15. customyielding 2.95 of crude product

Sources & evidence

ORD record
ord-ceedb682bbfa427cbb84077aff31cc67
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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