1,1'-Carbonyldiimidazole → N-(2,6-dihydroxyphenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide
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]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 3-cyclopentyloxy-4-methoxyphenylacetic acid (2.49 g) and 1,1′-carbonyl diimidazole (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), 1 N 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.
Workup
- stirringthe mixture stirred at room temperature, under argon, overnight
- extractionextracted with dichloromethane (3×50 ml)
- washThe combined organic extracts were washed with water (100 ml), 1 N HCl (100 ml) and brine (100 ml)
- dry with materialdried over CaSO4
- customevaporated in-vacuo
Sources & evidence
- ORD record
- ord-ea0e96dfe7394bd5898b22d01b27d81d
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06372770B1
Reaction notes
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