3,4-Dichlorobenzaldehyde → (E)-9-chloro-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine dihydrochloride

HRID 48325

反応式

HRID 48325 の反応式
C(OP([CH:9]=[C:10]1[NH:16][CH2:15][CH2:14][NH:13][C:12]2[C:17]([Cl:21])=[CH:18][CH:19]=[CH:20][C:11]1=2)(=O)OCC)C.[H-].[Na+].[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH:28]=O>O1CCCC1>[ClH:21].[ClH:24].[Cl:21][C:17]1[C:12]2[NH:13][CH2:14][CH2:15][N:16]=[C:10]([CH:9]=[CH:28][C:27]3[CH:30]=[CH:31][C:32]([Cl:33])=[C:25]([Cl:24])[CH:26]=3)[C:11]=2[CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 227103,4-DichlorobenzaldehydeHCID 24758Sodium hydrideHCID 86585810(9-Chloro-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester

生成物 1

HCID 136386025(E)-9-chloro-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine dihydrochloride収率 154.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 91 mg (0.275 mmol) of (9-chloro-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester in 2 ml of tetrahydrofuran was added 19 mg (0.48 mmol) of sodium hydride (60% dispersion in mineral oil). After 10 minutes 50 mg (0.29 mmol) of 3,4-dichlorobenzaldehyde was added and the mixture was stirred for 18 hours. The product was purified by column chromatography (20 g IST pre-packed column) eluting with 1% methanol/dichloromethane and treated with 0.10 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated to give 90 mg of (E)-9-chloro-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine dihydrochloride as an orange solid; MS: m/e 352.7 [M+H]+.

後処理

  1. customThe product was purified by column chromatography (20 g IST pre-packed column)
  2. washeluting with 1% methanol/dichloromethane
  3. additiontreated with 0.10 ml of 4M hydrogen chloride in dioxan
  4. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-892f4750b6e54144900dbfa3d7e151e6
出典データセット
uspto-grants-2004_03
特許番号
US06703387B2

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