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

HRID 1060025ノート

反応式

HRID 1060025 の反応式
[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]

参加物

6

反応物 4

HCID 9864CyanamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 186675631-Chloro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene

生成物 1

HCID 18667498N-cyano-4-(4-methoxypyridin-2-yl)-2-nitroaniline収率 89.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationfiltered
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-9ddb66a6987e4c3a98f13b59cef3053b
出典データセット
uspto-grants-2003_02
特許番号
US06521643B1

反応ノート

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