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

HRID 1756964Notes

Reaction equation

HRID 1756964 reaction equation
[CH2:1]([C:13]1[CH:17]=[C:16]([CH2:18][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].Cl.[CH3:23][O:24][C:25]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[C:26]=1[NH2:27].C(N(CC)CC)C>O1CCCC1.ClCCl>[CH2:1]([C:13]1[CH:17]=[C:16]([CH2:18][C:19]([NH:27][C:26]2[C:28]([O:34][CH3:35])=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:25]=2[O:24][CH3:23])=[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]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27644342,4,6-trimethoxyaniline HydrochlorideHCID 104941103-Dodecyl-5-isoxazole acetic acid

Product 1

HCID 106952922-(3-Dodecyl-isoxazol-5-yl)-N-(2,4,6-trimethoxy-phenyl)-acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, room temperature solution of 3-dodecyl-5-isoxazole acetic acid (0.64 g, 0.0022 mol) in dry tetrahydrofuran (20 mL) under nitrogen was added in one portion, 1,1-carbonyldiimidazole (0.38 g, 0.0024 mol), and the mixture was stirred for 2 hours. To this solution was added 2,4,6-trimethoxyaniline hydrochloride (0.48 g, 0.0022 mol) and triethylamine (0.33 mL, 0.0024 mol) in THF (30 mL). The mixture was stirred for 2 days and allowed to cool. The solution was rotoevaporated and the residue dissolved in dichloromethane. The solid was filtered through silica gel (77 g, 70-230 mesh) using petroleum ether-acetone (4:1, 35×75 mL) and the filtrate rotoevaporated to an oil. The oil was dried in vacuo. The oil crystallized to give a pale yellow waxy solid; yield 0.96 g (96%); mp 107°-109° C.

Workup

  1. stirringThe mixture was stirred for 2 days
  2. temperatureto cool
  3. filtrationThe solid was filtered through silica gel (77 g, 70-230 mesh)
  4. customThe oil was dried in vacuo
  5. customThe oil crystallized
  6. customto give a pale yellow waxy solid

Sources & evidence

ORD record
ord-b1bd25458f764b7080dcb4c5e616decc
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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