Hydrochloric Acid → HCID 59226943、化合物

HRID 888457ノート

反応式

HRID 888457 の反応式
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[CH3:27])=[O:8])=[CH:5][C:4]=1[N+:30]([O-])=O)#[N:2].[Sn](Cl)(Cl)(Cl)Cl.Cl.[OH-].[Na+]>COCCOCCOC>[NH2:30][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:3]=1[C:1]#[N:2])[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:23])([F:24])[F:25])[C:18]([F:19])([F:20])[F:21])=[CH:12][C:11]=1[CH3:27])=[O:8]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 59226970HCID 59226970、化合物

生成物 1

HCID 59226943HCID 59226943、化合物収率 51.3%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

反応条件

温度
0 °C

実験手順

4-Cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamide (1.0 g, 2.16 mmol) (Example D.) was dissolved in diethylene glycol dimethyl ether (“diglyme”) (25 ml) and tin chloride (1.229 g, 6.48 mmol) was added. The mixture was cooled to 0° C. and aqueous hydrochloric acid (concentrated) (4 ml) was added slowly. The reaction mixture was stirred at 80° C. for 0.5 hours. Aqueous sodium hydroxide (30% by weight) (80 ml) was added to adjust the pH to 7-8. The aqueous phase was extracted three times with ethyl acetate (200 ml). The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1 to 0:1) to give 3-amino-4-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.48 g, 51% yield). 1H-NMR (400 MHz, CDCl3): 7.54 (s, 1H), 7.49 (d, 2H), 7.36 (m, 3H), 7.15 (q, 1H), 2.3 (s, 6H) ppm.

後処理

  1. extractionThe aqueous phase was extracted three times with ethyl acetate (200 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1 to 0:1)

出典と根拠

ORDレコード
ord-5d0290a5a1cb46a48863fbdf55f92724
出典データセット
uspto-grants-2012_08
特許番号
US08247594B2

反応ノート

読み込み中…