Chloroacetaldehyde → 3-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole

HRID 38091

반응식

HRID 38091 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:12]([SH:15])[NH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:23][CH:24]=[O:25]>C1COCC1.O.CCOC(C)=O.C([O-])(O)=O.[Na+]>[OH:25][CH:24]1[CH2:23][S:15][C:12]2=[C:11]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:14][N:13]12

참가 물질

6

반응물 2

HCID 33ChloroacetaldehydeHCID 178526614HCID 178526614, 화합물

생성물 1

HCID 674426243-Hydroxy-6-(3-nitrophenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole수율 72.7%

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

5-(3-Nitro-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (prepared as described in Example 1) (3.92 g, 13.14 mmol) was dissolved in a 1:1 THF/water mixture (130 mL). Chloroacetaldehyde (55% in water, 2.31 mL, 19.71 mmol, 1.5 eq) was added and the solution was stirred at room temperature overnight. The reaction mixture was diluted with AcOEt and saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine, dried and evaporated to dryness. 3.25 g of crude product were obtained as yellow solid (72%), which was used in the following step without further purification.

후처리

  1. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. customevaporated to dryness

출처 및 근거

ORD 기록
ord-077782a335c4497a9139fd5fd4e839e6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524707B2

연결된 노트

불러오는 중…