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Triethylamine → 2-(3-Dodecyl-isoxazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 264113
Notes
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Reaction equation

HRID 264113 reaction equation
[CH2:1]([C:13]1[CH:17]=[C:16]([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([OH:21])=O)[O:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(C1ON=C(C(C2C=CC=CC=2)C(O)=O)C=1)CCCCCCCCCCC.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:68][O:69][C:70]1[CH:76]=[C:75]([O:77][CH3:78])[CH:74]=[C:73]([O:79][CH3:80])[C:71]=1[NH2:72].C(N(CC)CC)C>O1CCCC1>[CH2:1]([C:13]1[CH:17]=[C:16]([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([NH:72][C:71]2[C:73]([O:79][CH3:80])=[CH:74][C:75]([O:77][CH3:78])=[CH:76][C:70]=2[O:69][CH3:68])=[O:21])[O:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27644342,4,6-trimethoxyaniline HydrochlorideHCID 105232775-Dodecyl-alpha-phenyl-3-isoxazole acetic acidHCID 108330563-Dodecyl-alpha-phenyl-5-isoxazole acetic acid

Product 1

HCID 10075862
2-(3-Dodecyl-isoxazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature, stirred solution of 3-dodecyl-α-phenyl-5-isoxazole acetic acid and 5-dodecyl-α-phenyl-3-isoxazole acetic acid (48.42 g, 0.1303 mol) in dry tetrahydrofuran (1.4 L) was added in one portion 1,1'-carbonyldiimidazole (22.5 g, 0.139 mol), and the solution was stirred for 1.9 hours under nitrogen. To the mixture was added 2,4,6-trimethoxyaniline hydrochloride (28.5 g, 0.130 mol) and triethylamine (19 mL, 0.14 mol), and the mixture was stirred for 1.8 days under nitrogen. The mixture was rotoevaporated and partitioned between ethyl acetate and 1M HCl. The organic layer was washed (1M HCl; saturated NaCl), dried (MgSO4), and rotoevaporated to a tar. The tar was dissolved (THF) and repeatedly chromatographed on silica gel (230-400 mesh) using Heptane-ether-triethylamine-methanol (20:40:6:1) as eluent. Fractions containing pure compound were combined, rotoevaporated, dissolved in toluene, and reevaporated. The residue was crystallized from diisopropyl ether to give pure title compound; yield 17.6 g (25%); mp 107°-108° C.

Workup

  1. stirringthe mixture was stirred for 1.8 days under nitrogen
  2. custompartitioned between ethyl acetate and 1M HCl
  3. washThe organic layer was washed (1M HCl; saturated NaCl)
  4. dry with materialdried (MgSO4)
  5. dissolutionThe tar was dissolved (THF)
  6. customrepeatedly chromatographed on silica gel (230-400 mesh)
  7. additionFractions containing pure compound
  8. dissolutiondissolved in toluene
  9. customreevaporated
  10. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8eb9b27522d74d2cacf71566b5ab0ca2
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05646170

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes