Propylamine → 2-Amino-5-iodo-N-propylbenzamide
Reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[I:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:14]C(=O)O[C:11](=[O:16])[C:10]=2[CH:17]=1>N1C=CC=CC=1>[NH2:14][C:9]1[CH:8]=[CH:7][C:6]([I:5])=[CH:17][C:10]=1[C:11]([NH:4][CH2:1][CH2:2][CH3:3])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Propylamine (1.2 g, 20.3 mmol) and 6-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (5.0 g, 17.3 mmol) were combined in pyridine (85 mL) and stirred at room temperature for 24 h. The reaction was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate (200 mL) and 5% hydrochloric acid (200 mL). The phases were separated and the organic phase was washed with 1N sodium hydroxide, water, and brine. Drying over anhydrous sodium sulfate and evaporation under reduced pressure afforded 3.9 g of the title compound, 1H NMR (300 MHz, CDCl3): δ0.99 (t,3H1); 1.63 (m,2H); 3.35 (m,2H); 5.52 (br s,2H); 5.95 (br s,1H); 6.47 (d, 1H); 7.42 (dd,1H); 7.55(d,1H).