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

HRID 972236ノート

反応式

HRID 972236 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ceedb682bbfa427cbb84077aff31cc67
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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