N-Phenyl-p-phenylenediamine → N-[4-(phenylamino)phenyl]propanamide

HRID 1957337노트

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HRID 1957337 반응식
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>C(Cl)Cl>[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:20](=[O:23])[CH2:21][CH3:22])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 7564N-Phenyl-p-phenylenediamineHCID 62324Propionyl chlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 853805N-[4-(phenylamino)phenyl]propanamide수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A stirred mixture of 1.84 g (10.0 mmol, 1 eq.) of commercial N-phenyl-1,4-phenylenediamine (a black solid) and 1.18 g (14.0 mmol, 1.4 eq.) of NaHCO3 in 40 mL of CH2Cl2 was cooled to 0° C. To this suspension was added a solution of 0.96 mL (11.0 mmol, 1.1 eq.) of propionyl chloride in 10 mL of CH2Cl2 dropwise. The ice bath was removed and the mixture stirred for 1 hour and then poured into a seperatory funnel containing 50 mL of each CH2Cl2 and water. The organic phase was separated and extracted with 50 mL of saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (100 g SiO2, 1:1 ethyl acetate-hexanes) to give 1.79 g (75%) of product. 1H NMR (300 MHz, CDCl3) δ7.41 (d, 2H), 7.21-7.43 (m, 2H), 7.14 9 (bs, 1H), 6.96-7.07 (m, 4H) 6.90 (t, 1H), 5.66 (bs, 1H), 2.38 (q, 2H), 1.25 (t, 3H). MS (DCl) m/e 258 (M+NH4)+, 241 (M+H)+.

후처리

  1. customThe ice bath was removed
  2. additionpoured into a seperatory funnel
  3. additioncontaining 50 mL of each CH2Cl2 and water
  4. customThe organic phase was separated
  5. extractionextracted with 50 mL of saturated aqueous NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (100 g SiO2, 1:1 ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-eb320472994f448cae673f10bda317d3
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05783593

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