Thiourea → 2-amino-4H,5H,6H,7H,8H-cyclohepta[d][1,3]thiazol-8-one
Reaction equation
Br[CH:2]1[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:11][C:12]([NH2:14])=[S:13]>CCO>[NH2:14][C:12]1[S:13][C:2]2[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[N:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-bromocycloheptane-1,3-dione (45.17 mmol) in abs. EtOH (100 mL) was added thiourea (3.61 g, 47.43 mmol). The reaction mixture was stirred at room temperature overnight at which point the EtOH was removed under reduced pressure and the resulting dark orange residue was triturated with DCM. The residue was recrystallized from EtOH to afford 26z as an off white solid (6 g, 50% overall crude yield from cycloheptane-1,3-dione). 1H NMR (300 MHz, DMSO-d6): δ 8.87 (br s, 2H), 2.87 (t, J=6 Hz, 2H), 2.64 (t, J=6 Hz, 2H), 1.89-1.85 (m, 2H), 1.81-1.77 (m, 2H);