Cyanamide → N-cyano-4-(4-methoxypyridin-2-yl)-2-nitroaniline

HRID 1060025Notes

Reaction equation

[N:1]#[C:2][NH2:3].[H-].[Na+].Cl[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=2)=[CH:9][C:8]=1[N+:21]([O-:23])=[O:22].[Cl-].[NH4+]>CN(C)C=O>[C:2]([NH:3][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=2)=[CH:9][C:8]=1[N+:21]([O-:23])=[O:22])#[N:1]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of cyanamide (101 mg) in N,N-dimethylformamide (15 ml) was added sodium hydride (60% dispersion in mineral oil, 90 mg), and the resultant suspension was stirred at ambient temperature for 30 minutes. To the suspension was added 1-chloro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene (264 mg), and the mixture was stirred at 80° C. for 4 hours. The mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate three times. The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, filtered and dried under reduced pressure to give N-cyano-4-(4-methoxypyridin-2-yl)-2-nitroaniline (241 mg).

Workup

extractionextracted with ethyl acetate three times
washThe combined organic layer was washed with brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customThe residue was triturated with diisopropyl ether
filtrationfiltered
customdried under reduced pressure

Sources & evidence

ORD record: ord-9ddb66a6987e4c3a98f13b59cef3053b
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521643B1

Reaction notes

Loading…