Phosphorus trichloride → 2-Amino-5-(4-pyridyl)-4-[(4-piperonyl-1-piperazinyl)carbonyl]thiazole

HRID 648590노트

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HRID 648590 반응식
[CH2:1]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.P(Cl)(Cl)Cl.[NH2:21][C:22]1[S:23][C:24]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:25]([C:27](O)=[O:28])[N:26]=1>N1C=CC=CC=1>[NH2:21][C:22]1[S:23][C:24]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:25]([C:27]([N:14]2[CH2:15][CH2:16][N:11]([CH2:1][C:2]3[CH:10]=[CH:9][C:8]4[O:7][CH2:6][O:5][C:4]=4[CH:3]=3)[CH2:12][CH2:13]2)=[O:28])[N:26]=1

참가 물질

5

반응물 3

HCID 24387Phosphorus trichlorideHCID 944261-PiperonylpiperazineHCID 201449862-Amino-5-(pyridin-4-yl)-1,3-thiazole-4-carboxylic acid

생성물 1

HCID 201450812-Amino-5-(4-pyridyl)-4-[(4-piperonyl-1-piperazinyl)carbonyl]thiazole수율 19%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
80 °C

실험 절차

To a mixture of 1-piperonylpiperazine (2.72 g) and phosphorus trichloride (0.49 ml) in pyridine (20 ml) was added 2-amino-5-(4-pyridyl)-4-thiazolecarboxylic acid (1.24 g) and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The resultant mixture was adjusted to pH 8.0 with saturated aqueous potassium carbonate. The organic extract was dried over magnesium sulfate. The solvent was evaporated in vacuo to give a crystalline residue, which was recrystallized from ethyl acetate to afford 2-amino-5-(4-pyridyl)-4-[(4-piperonyl-1-piperazinyl)carbonyl]thiazole (0.45 g). mp 216°-217° C.

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customto give a crystalline residue, which
  7. customwas recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-1fb820e14d0449cf8bd37a69fee45a8d
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04735957

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