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

HRID 1383468Notes

Reaction equation

HRID 1383468 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 97983363-(cyclopentyloxy)-N-(2,6-difluorophenyl)-4-methoxybenzamideYield 46.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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,40%].

Workup

  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

Sources & evidence

ORD record
ord-43100ce3f48b45408d880665c718fa5b
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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