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 867530ノート

反応式

HRID 867530 の反応式
[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

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-7d3e1a0c5d244708aaea56a1331b7cb6
出典データセット
uspto-grants-1988_10
特許番号
US04775671

反応ノート

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