Acetic Anhydride → HCID 18542894, compound

Reaction equation

C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[C:13]([NH2:15])[CH:14]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[NH2:16][C:11]1[CH:12]=[C:13]([NH:15][C:5](=[O:7])[CH3:6])[CH:14]=[C:9]([Cl:8])[CH:10]=1

Participants

Procedure

DMAP (50 mg) and acetic anhydride (3.9 g, 37.9 mmol) were added sequentially and dropwise to a cold solution of 5-chloro-benzene-1,3-diamine (4.5 g, 31.6 mmol) in pyridine (22 mL) keeping the internal temperature below 0° C. The reaction mixture was allowed to warm to rt, stirred for 2 h, cooled to 0° C., quenched by addition of ice cooled water, and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH, 99:1) to afford the title compound. tR: 0.18 min (LC-MS 2); ESI-MS: 184.9 [M+H]+ (LC-MS 2); Rf=0.32 (hexane/EtOAc, 1:4).