Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(3-Cyclopentyloxy-4-methoxybenzyl)-4-hydroxybenzoxazole

HRID 1377548Notes

Reaction equation

HRID 1377548 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[NH:9][C:10](=[O:26])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:13]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1.O>[CH:21]1([O:20][C:14]2[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=2[O:18][CH3:19])[CH2:11][C:10]2[O:26][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=3[N:9]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22618291N-(2,6-dihydroxyphenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

Product 1

HCID 99677292-(3-Cyclopentyloxy-4-methoxybenzyl)-4-hydroxybenzoxazoleYield 51.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

A solution of N-(2,6-dihydroxyphenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide (2.10 g) and pyridinium p-toluene-sulphonate (532 mg) in xylene (100 ml) was refluxed, under nitrogen, overnight. The reaction mixture was cooled to room temperature, diluted with water (100 ml), and extracted with dichloromethane (3×75 ml). The combined organic extracts were washed with water (3×100 ml), brine (100 ml), dried (CaSO4) and evaporated in-vacuo to yield a pale brown solid. The solid was purified by flash chromatography (SiO2 ; dichloromethane;methanol (50:1)) to yield the title compound (1.027 g, 51%) as a white solid (mp 172°-181° C.). δH (250MHz;d6DMSO) 1.53-1.85 (8H,m,4×CH2), 3.70 (3H, s,OMe), 4.18 (2H,s,CH2), 4.72 (1H,m,CH), 6.69 (1H,dd,ArH), 6.82 (1H,dd,ArH), 6.89 (1H,d,ArH), 6.93 (1H,d,ArH), 7.02 (1H,dd,ArH), 7.11 (1H,t,ArH), 10.22 (1H,s,ArOH). m/z 339 (M+), 271 (M--C5H8), 256,242,228,199,149,137,123,94.

Workup

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washThe combined organic extracts were washed with water (3×100 ml), brine (100 ml)
  3. dry with materialdried (CaSO4)
  4. customevaporated in-vacuo
  5. customto yield a pale brown solid
  6. customThe solid was purified by flash chromatography (SiO2 ; dichloromethane;methanol (50:1))

Sources & evidence

ORD record
ord-24ad124d3fe84c4fb96507fc68afe816
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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