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Mercaptoacetonitrile → 11-Cyanomethylthio-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

HRID 232881
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반응식

HRID 232881 반응식
[SH:1][CH2:2][C:3]#[N:4].O[CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[CH:20][C:7]1=2>FC(F)(F)C(O)=O.C(Cl)Cl.C(OCC)(=O)C>[C:3]([CH2:2][S:1][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[CH:20][C:7]1=2)#[N:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 4346655MercaptoacetonitrileHCID 2335916711-Hydroxy-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

생성물 1

HCID 2335915911-Cyanomethylthio-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine수율 48.2%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매
HCID 8857
Ethyl Acetate
용매

실험 절차

Under ice cooling and stirring, 0.44 g of mercaptoacetonitrile was added to 2.22 g of 11-hydroxy-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 45 dissolved in a mixed solution of 20 ml of trifluoroacetic acid and 10 ml of methylene chloride and the mixture was stirred at the same temperature for 1.5 hours. The residue obtained by condensing the reaction mixture under reduced pressure was dissolved in ethyl acetate and the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated saline solution and dried over anhydrous sodium sulfate. The viscous residue obtained by removing the solvent was crystallized from diethyl ether to obtain 1.23 g of the title compound.

후처리

  1. customobtained in Reference example 45
  2. stirringthe mixture was stirred at the same temperature for 1.5 hours
  3. customThe residue obtained by condensing the reaction mixture under reduced pressure
  4. washthe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution
  5. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  6. customThe viscous residue obtained
  7. customby removing the solvent
  8. customwas crystallized from diethyl ether

출처 및 근거

ORD 기록
ord-90afd8ef592641ed97a12afedabac117
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05591752

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