Lawesson's reagent → (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

HRID 867530노트

반응식

HRID 867530 반응식
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:18])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)S2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 54153267(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

생성물 1

HCID 54287641(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 6.32 g (20 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide, 5.68 g (14 mmol) of 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide and 100 ml of toluene is heated to boiling under reflux for 4.5 hours. The solution obtained is then evaporated in vacuo and the residue is chromatographed on silica gel while eluting with ethyl acetate. After recrystallization from methylene chloride/ethyl acetate there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile of melting point 237°-238°.

후처리

  1. temperatureis heated
  2. temperatureunder reflux for 4.5 hours
  3. customThe solution obtained
  4. customis then evaporated in vacuo
  5. customthe residue is chromatographed on silica gel
  6. washwhile eluting with ethyl acetate
  7. customAfter recrystallization from methylene chloride/ethyl acetate there

출처 및 근거

ORD 기록
ord-7d3e1a0c5d244708aaea56a1331b7cb6
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04775671

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