Iodoethane → 2-Ethyl-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](I)[CH3:22]>CS(C)=O>[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)[CH3:22]Participants
Procedure
To a solution of (11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 9, 100 mg, 0.35 mmol) in DMSO was added ethyl iodide (28.2 μL, 0.35 mmol). The mixture was stirred at room temperature for 48 hr. DMSO was removed under vacuum and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was dried with magnesium sulfate, filtered and the solvent evaporated to give a yellow semi-solid which was chromatographed on silica gel (10% methanol/90% ethyl acetate) to give a yellow solid (109 mg, 55%). H1 NMR (DMSO d6) δ: 8.96 (s, 1H), 7.34 (s, 1H), 7.09-7.03 (m, 2H), 6.99-6.93 (m, 4H), 6.88-6.86 (m, 3H), 3.0-2.95 (q, 1H, J=7), 1.30-1.27 (t, 3H, J=7), MS (ES): MH+ 313.2.
Workup
- customDMSO was removed under vacuum
- customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
- dry with materialThe organic layer was dried with magnesium sulfate
- filtrationfiltered
- customthe solvent evaporated
- customto give a yellow semi-solid which
- customwas chromatographed on silica gel (10% methanol/90% ethyl acetate)
Sources & evidence
- ORD record
- ord-ccfaa2002b6a404d97fcd3340a9691ad
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06919328B1
Reaction notes
Loading…