Triethylamine → 3-(cyclopentyloxy)-N-(2,6-difluorophenyl)-4-methoxybenzamide

HRID 356885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356885
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].C(N(CC)CC)C.[CH:17]1([O:22][C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=2[O:32][CH3:33])[C:26](Cl)=[O:27])[CH2:21][CH2:20][CH2:19][CH2:18]1>ClCCl>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:23]([O:22][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[CH:24]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 796472,6-DifluoroanilineHCID 27946003-(Cyclopentyloxy)-4-methoxybenzoyl chloride

Produkt 1

HCID 97983363-(cyclopentyloxy)-N-(2,6-difluorophenyl)-4-methoxybenzamideAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A stirred solution of 2,6-difluoroaniline (1.52 g) and triethylamine (1.19 g) in dichloromethane (50 mL) at room temperature is treated dropwise with a solution of 3-cyclopentyloxy-4-methoxybenzoyl chloride (3.0 g), that is prepared as described hereinafter in Reference Example 3) in dichloro-methane (50 mL). The solution is stirred and heated at reflux for 4 hours, then it is cooled, washed with water and dried over magnesium sulfate. The solution is concentrated and the resulting residue is recrystallized from ethyl acetate, to give N-(2,6-difluorophenyl)-3-cyclopentyloxy-4-methoxybenzamide (1.9 g), m.p. 158°-160° C. [NMR(CDCl3):1.55-1.7(m,3H),1.8-2.05(m,5H), 3.93(s,3H),4.85(m,1H),6.9(d,1H),6.95-7.03(m,2H),7.2-7.3(m,1H),7.35(bs,1H), 7.45(q,1H),7.53(d,1H); Elemental analysis: C,65.1; H,5.6;F,10.4; N,4.2%; Calculated: C,65.7; H,5.5;F,10.9; N,4.0%]-

Aufarbeitung

  1. customis prepared
  2. temperatureheated
  3. temperatureat reflux for 4 hours
  4. temperatureit is cooled
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solution is concentrated
  8. customthe resulting residue is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5624aec227a548fd86add09b584bef64
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840724

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