1,1'-Carbonyldiimidazole → N-(2,6-dihydroxyphenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

HRID 1377547Notes

Reaction equation

HRID 1377547 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]([OH:18])=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:31][C:32]1[C:38]([OH:39])=[CH:37][CH:36]=[CH:35][C:33]=1[OH:34]>ClCCl.O>[OH:34][C:33]1[CH:35]=[CH:36][CH:37]=[C:38]([OH:39])[C:32]=1[NH:31][C:16](=[O:18])[CH2:15][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 694512-AminoresorcinolHCID 107293423-Cyclopentyloxy-4-methoxyphenylacetic acid

Product 1

HCID 22618291N-(2,6-dihydroxyphenyl)-3-cyclopentyloxy-4-methoxyphenylacetamideYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 3-cyclopentyloxy-4-methoxyphenylacetic acid (2.49 g) and 1,1'-carbonyldiimidazole (2.31 g) in dichloromethane (10 ml) was stirred at room temperature, under argon, for 2 hours. The resulting solution was added to a stirred suspension of 2-aminoresorcinol (1.62 g) in dichloromethane (15 ml) and the mixture stirred at room temperature, under argon, overnight. The reaction mixture was diluted with water (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were washed with water (100 ml), 1N HCl (100 ml) and brine (100 ml), dried over CaSO4 and evaporated in-vacuo to yield the title compound (2.122 g, 60%) as a beige solid. δH (250MHz;d6DMSO) 1.53-1.95 (SH,m,4×CH2), 3.65 (2H, s,CH2), 3.70 (3H,s,OMe), 4.75 (1H,m, CH), 6.3 (1H,s,ArH), 6.35 (1H,s,ArH), 6.90 (4H,m,ArH), 9.40 (2H,s,ArOH), 9.6 (1H,s,CONH).

Workup

  1. stirringthe mixture stirred at room temperature, under argon, overnight
  2. extractionextracted with dichloromethane (3×50 ml)
  3. washThe combined organic extracts were washed with water (100 ml), 1N HCl (100 ml) and brine (100 ml)
  4. dry with materialdried over CaSO4
  5. customevaporated in-vacuo

Sources & evidence

ORD record
ord-5ec2ccbd8c5a4d6f9eadd35a35f9f4d6
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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