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

HRID 38091

反応式

HRID 38091 の反応式
[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

参加物

6

反応物 2

HCID 33ChloroacetaldehydeHCID 178526614HCID 178526614、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-077782a335c4497a9139fd5fd4e839e6
出典データセット
uspto-grants-2013_09
特許番号
US08524707B2

関連ノート

読み込み中…