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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
Notes
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Reaction equation

HRID 48330 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-e3db9b8b46ee4afa84e47cc28b26c4e1
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06703387B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes