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Hydrochloric Acid → (E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride

HRID 48330
ノート
印刷プレビュー

反応式

HRID 48330 の反応式
[ClH:1].Cl.[CH2:3]([S:10][C:11]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][C:12]=1[CH:13]=[CH:14][C:15]1=[N:16][CH2:17][CH2:18][N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]1=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Sn](Cl)[Cl:35].Cl>O1CCCC1.C(O)C>[ClH:35].[ClH:1].[CH2:3]([S:10][C:11]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:12]=1/[CH:13]=[CH:14]/[C:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]([CH3:26])[CH2:18][CH2:17][N:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 69893360(E)-5-(2-benzylthio-5-nitrostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepine dihydrochloride

生成物 1

HCID 22742398(E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride収率 19.5%

試薬・触媒・溶媒 2

HCID 702Ethanol
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To 215 mg (0.50 mmol) of (E)-5-(2-benzylthio-5-nitrostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepine dihydrochloride (prepared as described in Example 15) in 8 ml of tetrahydrofuran and 8 ml of ethanol was added 380 mg (0.90 mmol) of tin (II) chloride and 0.48 ml of concentrated hydrochloric acid. The mixture was heated at 60° C. for 7 hours. The solution was reduced to half volume and partitioned between 50 ml of saturated sodium hydrogen carbonate solution and 100 ml and 50 ml of dichloromethane. The combined organic phases were dried (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography eluting with 2-5% methanol/dichloromethane and treated with 0.30 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated and the residue was recrystallised from methanol/ether to give 46 mg of (E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride as dark red crystals; MS: m/e 400 [M+H]+.

後処理

  1. custompartitioned between 50 ml of saturated sodium hydrogen carbonate solution and 100 ml and 50 ml of dichloromethane
  2. dry with materialThe combined organic phases were dried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with 2-5% methanol/dichloromethane
  7. additiontreated with 0.30 ml of 4M hydrogen chloride in dioxan
  8. customThe solvent was evaporated
  9. customthe residue was recrystallised from methanol/ether

出典と根拠

ORDレコード
ord-e3db9b8b46ee4afa84e47cc28b26c4e1
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06703387B2

反応ノート

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