Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(3-Cyclopentyloxy-4-methoxybenzyl)-7-nitrobenzoxazole

HRID 1377545Notes

Reaction equation

HRID 1377545 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:15]=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:23]1([O:22][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=2[O:20][CH3:21])[CH2:13][C:12]2[O:28][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=3[N:11]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22618278N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

Product 1

HCID 101095852-(3-Cyclopentyloxy-4-methoxybenzyl)-7-nitrobenzoxazoleYield 58.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

A solution of N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide (2.0 g) and pyridinium p-toluene-sulphonate (500 mg) in xylene (140 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 an orange oil. The oil was purified by flash chromatography (SiO2 ;dichloromethane;ethanol;ammonia (50:1:0.1)) to yield the title compound (1.107 g, 58%) as an orange solid (top 95°-98.5° C.). δH (250 MHz;d6DMSO) 1.45-1.95 (8H,m,4×CH2), 3.70 (3H,s,OMe), 4.36 (2H, s,CH2), 4.74 (1H,m,CH), 6.89 (2H,bs,ArH), 7.02 (1H,bs,ArH), 7.56 (1H,t,ArH), 8.15 (1H,dd,ArH), 8.17 (1H,dd,ArH). m/z 368 (M+), 338 (M--NO), 300 (M--C5H8), 285, 270, 253, 149, 137, 123, 100.

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 an orange oil
  6. customThe oil was purified by flash chromatography (SiO2 ;dichloromethane;ethanol;ammonia (50:1:0.1))

Sources & evidence

ORD record
ord-1fb81cef3c9e44a58ac7adb84bee023a
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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