Water → 2-(Octylthio)thiazole-4-carboxylic acid ethyl ester

HRID 128815

반응식

HRID 128815 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([SH:11])[S:9][CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([S:11][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[S:9][CH:10]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 178470113HCID 178470113, 화합물

생성물 1

HCID 545268652-(Octylthio)thiazole-4-carboxylic acid ethyl ester수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-mercaptothiazole-4-carboxylic acid ethyl ester (Zhelyazkov, L.; Todorova, N.; Manolova, P. Tr. Nauchnoizsled. Khim.-Farm. Inst., 9, 59-67 (1974); Chem. Abstr., 83, 58706 q) (3.0 g) in DMF (20 ml) is added sodium hydride (0.70 g of 60% dispersion). After 10 min, 1-bromooctane (3.0 ml) is added, and the mixture is stirred at 60° for 30 min. The mixture is poured into water and extracted with ether, and the extracts are dried, filtered, and concentrated. The residue is recrystallized from hexane to provide 2-(octylthio)thiazole-4-carboxylic acid ethyl ester as a colorless solid (3.7 g, 78%). This material is reduced in the usual fashion with lithium aluminum hydride in THF, providing 2-(octylthio)thiazole-4-methanol (2.12 g, 67%) as a colorless oil after chromatography. This is combined with DDQ (1.8 g) in 1,4-dioxane (25 ml) and stirred for 48 hr at room temperature. The reaction mixture is filtered, and the filtrate is concentrated and chromatographed with dichloromethane to provide 2-(octylthio)thiazole-4-carboxaldehyde as a tan solid (1.67 g, 81%).

후처리

  1. extractionextracted with ether
  2. customthe extracts are dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is recrystallized from hexane

출처 및 근거

ORD 기록
ord-98e1c24e5a604cc69a49499f9b1264e5
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

연결된 노트

불러오는 중…