Methanol → 2-Benzyl-1-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-isothiourea
Reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]2[CH:13]=[CH:14][C:15]([NH:17][C:18]([NH2:20])=[S:19])=[CH:16][C:3]1=2.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.ClCCl.CO>CN(C=O)C>[CH2:21]([S:19][C:18](=[NH:20])[NH:17][C:15]1[CH:14]=[CH:13][C:4]2[NH:5][C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[NH:8][C:2](=[O:1])[C:3]=2[CH:16]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 9, 50 mg, 0.18 mmol) in DMF (1 mL) was added benzyl bromide (21 μL, 0.18 mmol). The solution was stirred at room temperature for 2 hr then heated at 60° C. for 1 hr. The solvent was removed under vacuo. The residue was dissolved in a mixture of tetrahydrofuran (5 mL) and diethyl ether (5 mL) and treated with 2 mL of saturated sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulfate and evaporated to give an oily residue which was subjected to silica gel column chromatography (98% dichloromethane: 2% methanol). H1 NMR (acetone d6) δ: 8.91 (bs, 1H), 7.42-7.21 (m, 5H), 7.09-6.89 (m, 7H), 5.93 (bs, 1H), 4.31 (s, 2H).
Workup
- temperaturethen heated at 60° C. for 1 hr
- customThe solvent was removed under vacuo
- dissolutionThe residue was dissolved in a mixture of tetrahydrofuran (5 mL) and diethyl ether (5 mL)
- additiontreated with 2 mL of saturated sodium bicarbonate solution
- customThe organic layer was separated
- dry with materialdried over magnesium sulfate
- customevaporated
- customto give an oily residue which
Sources & evidence
- ORD record
- ord-2a47fa2e0f1144309b72a14237d598b1
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06919328B1
Reaction notes
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