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2-Amino-4,5-dimethoxybenzonitrile → Prazosin

HRID 1576327
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HRID 1576327 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.C1([Li])C=CC=CC=1.[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]([C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)=[O:30])[CH2:25][CH2:24]1)#[N:22]>C1C=CC=CC=1.C(OCC)C>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([O:12][CH3:13])=[C:5]([O:10][CH3:11])[CH:6]=2)[N:1]=[C:21]([N:23]2[CH2:24][CH2:25][N:26]([C:29]([C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)=[O:30])[CH2:27][CH2:28]2)[N:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7359672-Amino-4,5-dimethoxybenzonitrileHCID 130593091-Cyano-4-(2-furoyl)piperazineHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 4893Prazosin

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 3283Diethyl Ether용매

실험 절차

To 3.6 g. of 6-aminoveratronitrile, dissolved in 75 ml. of anhydrous benzene, a solution of phenyl lithium (prepared from 0.35 g. of lithium and 3.9 g. of bromobenzene) in 60 ml. of anhydrous diethyl ether is added under a nitrogen atmosphere. After 45 minutes 4.4 g. of 1-cyano-4-(2-furoyl)piperazine in 50 ml. of anhydrous benzene are added. The ether and part of the benzene are distilled off and 100 ml. of tetrahydrofuran are added. The mixture is refluxed under the nitrogen atmosphere for 20 hours and then decomposed with water. The liquid is distilled off and 75 ml. of water are added to the residue. The mixture is extracted with chloroform and the extract is concentrated by evaporation of the solvent. 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)4-(2-furoyl)piperazine is obtained. The product after crystallization from a mixture of ethanol and water melts at 258°-260°C.

후처리

  1. distillationThe ether and part of the benzene are distilled off
  2. additionof tetrahydrofuran are added
  3. temperatureThe mixture is refluxed under the nitrogen atmosphere for 20 hours
  4. distillationThe liquid is distilled off
  5. additionof water are added to the residue
  6. extractionThe mixture is extracted with chloroform
  7. concentrationthe extract is concentrated by evaporation of the solvent

출처 및 근거

ORD 기록
ord-125d9c43bad14efbb614cbf75ead5e2c
출처 데이터셋
uspto-grants-1976_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03980650

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