Chloroacetaldehyde → 2-(Thiazol-2-ylamino)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one
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.Cl[CH2:22][CH:23]=O>C(O)C>[S:19]1[CH:23]=[CH:22][N:20]=[C:18]1[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]=1Participants
4
Procedure
To a solution of (11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 9, 75 mg, 0.26 mmol) in ethanol (10 mL) was added chloroacetaldehyde (50% in water, 0.1 mL). The solution was refluxed for 5 hr and then concentrated under vacuum and poured into water (5 mL). The solution pH was adjusted to 9 with aqueous saturated sodium bicarbonate and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent evaporated. The residue was recrystallized from ethanol/hexanes to give yellow solid (30 mg, 40%).