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Propargyl alcohol → 5,11-Dihydro-11-[[(2-propynyl)oxy]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 4170
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HRID 4170 반응식
C([Li])CCC.[CH2:6]([OH:9])[C:7]#[CH:8].Cl[C:11]([N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17](=[O:24])[NH:16][C:15]2[CH:25]=[CH:26][CH:27]=[N:28][C:14]1=2)=[O:12]>CCCCCC.O1CCCC1>[CH2:6]([O:9][C:11]([N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17](=[O:24])[NH:16][C:15]2[CH:25]=[CH:26][CH:27]=[N:28][C:14]1=2)=[O:12])[C:7]#[CH:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7859Propargyl alcoholHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 178418339Butyllithium

생성물 1

HCID 137292085,11-Dihydro-11-[[(2-propynyl)oxy]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 8058
Hexane
용매

실험 절차

At 15° to 20° C., 3.08 g (0.048 mol) of n-butyl-lithium in 30 ml of n-hexane are added dropwise to a solution of 2.24 g (0.04 mol) of propargyl alcohol in 120 ml of tetrahydrofuran. After it has all been added, the mixture is stirred for a further 30 minutes at ambient temperature and then mixed with a suspension of 10.9 g (0.04 mol) of 11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 250 ml of tetrahydrofuran. In order to complete the reaction the mixture is stirred for a further hour. It is evaporated to dryness in vacuo and the residue is crystallised by stirring in water. After recrystallisation from ethyl acetate, 7.5 g (64% of theory) of the desired product are obtained, m.p. 213° C.

후처리

  1. additionall been added
  2. customthe reaction the mixture
  3. stirringis stirred for a further hour
  4. customIt is evaporated to dryness in vacuo
  5. customthe residue is crystallised
  6. stirringby stirring in water
  7. customAfter recrystallisation from ethyl acetate, 7.5 g (64% of theory) of the desired product
  8. customare obtained

출처 및 근거

ORD 기록
ord-b62934e97d654247b2961e7c9f60d869
출처 데이터셋
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04724236

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