Sodium amide → 7-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606953ノート

反応式

HRID 1606953 の反応式
[Cl-].[Cl:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[Cl:25][C:26]1[C:31]2[C:32](=[O:43])[N:33]([CH3:42])[CH2:34][C:35]3[N:36]([CH:37]=[N:38][C:39]=3[CH:40]=O)[C:30]=2[CH:29]=[CH:28][CH:27]=1>O1CCCC1>[Cl:25][C:26]1[C:31]2[C:32](=[O:43])[N:33]([CH3:42])[CH2:34][C:35]3[N:36]([CH:37]=[N:38][C:39]=3/[CH:40]=[CH:3]\[Cl:2])[C:30]=2[CH:29]=[CH:28][CH:27]=1

参加物

5

反応物 3

HCID 24533Sodium amideHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 198515847-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

生成物 1

HCID 867433557-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

100 g of an equimolar mixture of chloromethyltriphenylphosphonium chloride and sodium amide were stirred for 45 minutes in 450 ml of tetrahydrofuran, whereby the temperature rose to 37°. 62.23 g (229.7 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde were then added portionwise thereto at room temperature and, after completion of the addition, the mixture was stirred for a further 1 hour. The reaction mixture was subsequently filtered and the filtrate was evaporated. After chromatography of the residue on silica gel while eluting with cyclohexane/ether/wasopropanol (3:3:1) there was obtained 7-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 205°-207°.

後処理

  1. customrose to 37°
  2. additionat room temperature and, after completion of the addition
  3. filtrationThe reaction mixture was subsequently filtered
  4. customthe filtrate was evaporated
  5. washAfter chromatography of the residue on silica gel while eluting with cyclohexane/ether/wasopropanol (3:3:1) there

出典と根拠

ORDレコード
ord-4e6d176c92604bb192e57a7ddecd8b8f
出典データセット
uspto-grants-1989_09
特許番号
US04863920

反応ノート

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