Phosphorus pentachloride → HCID 178466243、化合物

HRID 2074458ノート

反応式

HRID 2074458 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12](=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl.O.[OH-].[NH4+]>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:12]2[NH:1][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=3[N:11]=2)=[CH:15][CH:16]=1)[CH3:22]

参加物

6

反応物 2

HCID 24819Phosphorus pentachlorideHCID 59799754N-(2-Amino-5-nitro-phenyl)-2-(4-ethoxy-phenyl)-acetamide

生成物 1

HCID 178466243HCID 178466243、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒2 回HCID 14923Ammonium Hydroxide溶媒

実験手順

N-(2-Amino-5-nitro-phenyl)-2-(4-ethoxy-phenyl)-acetamide 41 (590 mg, 1.871 mmol), Phosphorous pentachloride (390 mg, 1.871 mmol) were dissolved in anhydrous chloroform (20 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. The solution was heated to reflux in an oil bath for 4 hours and cooled to room temperature overnight. The mixture was diluted with H2O and chloroform and 2M ammonium hydroxide solution added to adjust pH to 9-10. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with chloroform and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated to afford crude. The product was purified using dry silica gel column chromatography eluting with 20 mL portions of solvent system (2.5% 2M NH3 in methanol/95% dichloromethane) to afford a yellow residue 42 2-(4-Ethoxy-benzyl)-5-nitro-1H-benzimidazole. 1H NMR (DMSO) δ: 1.30 (t, 3H, J=6.5), 3.87 (q, 2H, J=7.3), 4.11 (s, 2H), 6.88 (d, 2H, J=8.0), 7.25 (d, 2H, J=7.9), 7.65 (d, 1H, J=8.9), 8.07 (d, 1H, J=9.0), 8.36-8.40 (m, 1H); MS (ESI): 298 (MH+, 100%)

後処理

  1. customfitted with an condenser
  2. temperatureThe solution was heated
  3. temperatureto reflux in an oil bath for 4 hours
  4. additionadded
  5. customThe mixture was transferred to a separatory funnel
  6. customthe organic layer collected
  7. extractionThe aqueous layer was further extracted with chloroform
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto afford crude
  13. customThe product was purified
  14. washeluting with 20 mL portions of solvent system (2.5% 2M NH3 in methanol/95% dichloromethane)

出典と根拠

ORDレコード
ord-a2b153bcfa3a4c59a9c0c9974527216f
出典データセット
uspto-grants-2011_04
特許番号
US07919510B2

反応ノート

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