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

HRID 842095
Notes
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Reaction equation

HRID 842095 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 7237
O-Xylene
Solvent

Procedure

A solution of N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxy-phenylacetamide (2.0 g) and pyridinium p-toluene-sulphonate (500 mg) in xylene (140 ml) was heated at reflux, under nitrogen, overnight. The reaction mixture was cooled to room temperature, diluted with water (100 ml) and extracted with dichloro-methane (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 (mp 95-98.5° C.).

Workup

  1. temperatureat reflux, under nitrogen, overnight
  2. extractionextracted with dichloro-methane (3×75 ml)
  3. washThe combined organic extracts were washed with water (3×100 ml), brine (100 ml)
  4. dry with materialdried (CaSO4)
  5. customevaporated in-vacuo
  6. customto yield an orange oil
  7. customThe oil was purified by flash chromatography (SiO2; dichloromethane; ethanol; ammonia (50:1:0.1))

Sources & evidence

ORD record
ord-eb3593b26aae4ac69d398faf77be4b96
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06372770B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes