Dimethyl-1,3-thiazole-5-carboxylic acid → HCID 67495517, 화합물

HRID 2365238노트

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HRID 2365238 반응식
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Li]CCCC.[CH3:16][N:17]1[C:21]([CH:22]=[O:23])=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:19]=[N:18]1>C1COCC1>[OH:23][CH:22]([C:21]1[N:17]([CH3:16])[N:18]=[N:19][C:20]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH2:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

참가 물질

5

반응물 3

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 86664842HCID 86664842, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67495517HCID 67495517, 화합물수율 83.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-75 °C

실험 절차

To a suspension of 2,4-dimethylthiazole-5-carboxylic acid (157 mg, 1.0 mmol) in THF (8 mL) was added dropwise n-BuLi (1.6 M in hexanes, 1.25 mL, 2.0 mmol) under Ar at −75° C. The brown suspension was stirred at −75° C. for 2 h and then a solution of 3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazole-4-carbaldehyde (188 mg, 1.0 mmol) in THF (3 mL) was added at −75° C. and the brown suspension was stirred at −75° C. for 2 h. The mixture was then quenched with an aqueous solution of citric acid (5%, 10 mL), allowed to warm to room temperature. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by recrystallisation from ethylacetate-heptane afforded the title compound (288 mg, 83%) as a light red solid. MS: m/e=344.0 [M−H]−.

후처리

  1. stirringthe brown suspension was stirred at −75° C. for 2 h
  2. customThe mixture was then quenched with an aqueous solution of citric acid (5%, 10 mL)
  3. temperatureto warm to room temperature
  4. additionThe mixture was then poured into saturated ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customPurification
  11. customby recrystallisation from ethylacetate-heptane

출처 및 근거

ORD 기록
ord-583922f8c6a04cf5b1f626b46a4fdfd2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697696B2

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