3,4-Dichlorobenzaldehyde → (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-8-(3-methoxyphenyl)-1-methyl-1H-1,4-benzodiazepine dihydrochloride

HRID 48334

反応式

HRID 48334 の反応式
C(OP([CH:9]=[C:10]1[NH:16][CH2:15][CH2:14][N:13]([CH3:17])[C:12]2[CH:18]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[CH:20]=[CH:21][C:11]1=2)(=O)OCC)C.[H-].[Na+].[Cl:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH:36]=O>O1CCCC1>[ClH:32].[ClH:32].[Cl:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH:36]=[CH:9][C:10]1=[N:16][CH2:15][CH2:14][N:13]([CH3:17])[C:12]2[CH:18]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)[CH:20]=[CH:21][C:11]1=2

参加物

5

反応物 3

HCID 227103,4-DichlorobenzaldehydeHCID 24758Sodium hydrideHCID 86585814[8-(3-Methoxyphenyl)-1-methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl]phosphonic acid diethyl ester

生成物 1

HCID 69892835(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-8-(3-methoxyphenyl)-1-methyl-1H-1,4-benzodiazepine dihydrochloride収率 58.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 100 mg (0.24 mmol) of [8-(3-methoxyphenyl)-1-methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl]phosphonic acid diethyl ester in 2 ml of tetrahydrofuran was added 17 mg (0.42 mmol) of sodium hydride (60% dispersion in mineral oil). After 10 minutes 44 mg (0.25 mmol) of 3,4-dichlorobenzaldehyde was added and the mixture was stirred for 3 hours. The product was purified by column chromatography (20 g IST pre-packed column) eluting with 1% methanol/ethyl acetate and treated with 0.10 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated to leave a red gum which was recrystallized from ethyl acetate to give 25 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-8-(3-methoxyphenyl)-1-methyl-1H-1,4-benzodiazepine dihydrochloride as an orange solid; MS: m/e 436 (M+).

後処理

  1. customThe product was purified by column chromatography (20 g IST pre-packed column)
  2. washeluting with 1% methanol/ethyl acetate
  3. additiontreated with 0.10 ml of 4M hydrogen chloride in dioxan
  4. customThe solvent was evaporated
  5. customto leave a red gum which
  6. customwas recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-384df9c5842547d1abb3c05ef1318876
出典データセット
uspto-grants-2004_03
特許番号
US06703387B2

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