Ethane, 2-bromo-1,1-diethoxy- → HCID 12036785, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH2:13])=[S:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14](OC(OCC)CBr)[CH3:15]>C(O)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[S:12][CH:14]=[CH:15][N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a suspension of 1-(4-nitrophenyl)-2-thiourea (5.00 g, 25.4 mmol) in acetic acid (40 mL) was added bromoacetaldehyde diethyl acetal (3.94 mL, 25.4 mmol) at RT. The resulting mixture was heated to 100° C. for 2 h. After cooling to RT, the solvent was removed in vacuo. The residue was diluted with 1M NaOH (100 mL) and EtOAc (100 mL). The phases were separated, and the aqueous phase was extracted with EtOAc (2×100 mL). The combined organic extracts were dried over MgSO4 and concentrated. Purification by column chromatography (20-80% EtOAc in hexanes) afforded the product as a yellow solid (2.75 g, 49%). 1H-NMR (400 MHz, DMSO-d6) δ 11.02 (s, 8.231H), 8.23 (d, J=9.3 Hz, 2H), 7.85 (d, J=9.3 Hz, 2H), 7.41 (d, J=3.6 Hz, 1H), 7.15 (d, J=3.6 Hz, 1H). LC/MS (10-99%) M/Z: M+1 obs=222.1; tR=2.50 min.