2-Amino-N-methylbenzamide → HCID 59516637, compound
Reaction equation
CO[C:3]1[C:8]([C:9]([C:11](=[C:17](SC)SC)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:7][N:6]=[C:5]([S:22][CH3:23])[N:4]=1.[NH2:24][C:25]1[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=1[C:27]([NH:29][CH3:30])=[O:28]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12]([C:11]1[C:9](=[O:10])[C:8]2[CH:7]=[N:6][C:5]([S:22][CH3:23])=[N:4][C:3]=2[N:24]2[C:17]=1[N:29]([CH3:30])[C:27](=[O:28])[C:26]1[CH:31]=[CH:32][CH:33]=[CH:34][C:25]2=1)=[O:13])[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A solution of ethyl 2-(4-methoxy-2-(methylthio)pyrimidine-5-carbonyl)-3,3-bis(methylthio)acrylate (775 mg, 2.069 mmol) and 2-amino-N-methylbenzamide (475 mg, 3.163 mmol) in toluene (5 mL) was heated over stream of nitrogen allowing toluene to evaporate and continued heating as neat at 140° C. for over night. Cooled to rt and precipitate formed from DCM (10 mL) was filtered off. The solvent of mother liquor was removed under reduced pressure and repeated the precipitation process with Et2O (10 mL). Trituration in methanol (10 mL) afforded the desired product as a yellow solid (30 mg, 4 %). MS (m/z): 397 (MH+). 1H NMR (CDCl3) δ: 9.37 (s, 1H), 8.37 (d, 1H), 8.26 (dd, 1H), 7.70 (m, 1H), 7.49 (m, 1H), 4.46 (q, 2H), 3.61 (s, 3H), 2.60 (s, 3H), 1.43 (t, 3H).