Hydrochloric Acid → 3-(1-Methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile

HRID 230086

반응식

HRID 230086 반응식
[C:1]([CH2:3][C:4]1[N:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:7][CH:8]=1)#[N:2].C([Li])CCC.[CH3:20][N:21]1[C:25]([Cl:26])=[C:24]([C:27](Cl)=[O:28])[C:23]([Cl:30])=[N:22]1.Cl>C1COCC1>[CH3:20][N:21]1[C:25]([Cl:26])=[C:24]([C:27]([OH:28])=[C:3]([C:4]2[N:5]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:7][CH:8]=2)[C:1]#[N:2])[C:23]([Cl:30])=[N:22]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 2238442-(2-Phenyl-1,3-thiazol-4-yl)acetonitrileHCID 221694993,5-Dichloro-1-methylpyrazole-4-carbonyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 569875153-(1-Methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-60 °C

실험 절차

0.72 g of 4-cyanomethyl-2-phenylthiazole was dissolved in 10 ml of dry THF, and 4.6 ml of n-butyl lithium (1.56 M hexane solution) was dropwise added thereto at −60° C. or lower in an argon atmosphere. After the resulting product was stirred at −60° C. or lower for 20 minutes, 0.84 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride as dissolved in 3 ml of dry THF was dropwise added thereto at −60° C. or lower. Then, the resulting product was gradually heated, and stirred for 4 hours at room temperature. The reaction mixture was poured into ice water, acidified with diluted hydrochloric acid, extracted with ethyl acetate, and washed with saturated saline. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain the intended product from the fraction eluted with chloroform. The resulting product was crystallized and washed with diethyl ether to obtain 0.8.6 g of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile.

후처리

  1. customat −60° C.
  2. additionwas dropwise added
  3. customat −60° C.
  4. temperatureThen, the resulting product was gradually heated
  5. stirringstirred for 4 hours at room temperature
  6. extractionextracted with ethyl acetate
  7. washwashed with saturated saline
  8. dry with materialThe resulting product was dried over sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residual product was purified through silica gel column chromatography
  11. customto obtain the intended product from the fraction
  12. washeluted with chloroform
  13. customThe resulting product was crystallized
  14. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-5baa66b8e90b4415b4735e96fe7a8474
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566683B2

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