Isobutylamine → N-isobutyl 3-phenylbenzamide

HRID 2421588

반응식

HRID 2421588 반응식
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:22]([NH2:26])[CH:23]([CH3:25])[CH3:24]>C1COCC1.CN(C=O)C>[CH2:22]([NH:26][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=1)[CH:23]([CH3:25])[CH3:24]

참가 물질

5

반응물 3

HCID 6558IsobutylamineHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 65578Oxalyl chloride

생성물 1

HCID 67214645N-isobutyl 3-phenylbenzamide

시약·촉매·용매 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

실험 절차

Oxalyl chloride (132 μL, 1.5 mmol) was added over a 10 minute period to a mixture of 3-phenylbenzoic acid (200 mg, 1 mmol) dissolved in a mixture THF/DMF (3.5 mL/58 μL). After the addition, the reaction was stirred at room temperature for 2.5 hours. Isobutylamine (247 μL, 2.5 mmol) was then added into half of the acid chloride solution at 0° C. The reaction was then stirred at room temperature for 18 hours. The reaction was concentrated and water was added to the residue. The aqueous phase was extracted 3 times with CH2Cl2. The combined organic layers were washed with 2N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. Diethyl ether was added to the residue and a white solid precipitated. It was collected by filtration and rinsed with a small amount of diethyl ether. The white solid was then dried under vacuum (102 mg, 71%). NMR 1H (ppm, CDCl3): 7.97 (t, J4=1.71 Hz, 1H), 7.70 (dd, J3=7.65 Hz, J4=1.77 Hz, 2H), 7.62-7.58 (m, 2H), 7.51-7.34 (m, 4H), 6.18 (br. s., 1H), 3.33-3.29 (m, 2H), 1.91 (n, J3=6.71 Hz, 1H), 0.98 (d, J3=6.68 Hz, 6H).

후처리

  1. additionAfter the addition
  2. stirringThe reaction was then stirred at room temperature for 18 hours
  3. concentrationThe reaction was concentrated
  4. additionwater was added to the residue
  5. extractionThe aqueous phase was extracted 3 times with CH2Cl2
  6. washThe combined organic layers were washed with 2N HCl, saturated NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. additionDiethyl ether was added to the residue
  10. customa white solid precipitated
  11. filtrationIt was collected by filtration
  12. washrinsed with a small amount of diethyl ether
  13. customThe white solid was then dried under vacuum (102 mg, 71%)

출처 및 근거

ORD 기록
ord-a1cd006b251f4eb695fc069fe7688c77
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956216B2

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