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

HRID 2380523Notes

Reaction equation

HRID 2380523 reaction equation
[CH2:1]([C:13]1[CH:17]=[C:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[C:28]=1[N:37]=[C:38]=[O:39].Cl.CCOCC>O1CCCC1.C([Li])CCC>[CH2:1]([C:13]1[CH:17]=[C:16]([CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:38]([NH:37][C:28]2[C:29]([O:35][CH3:36])=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:27]=2[O:26][CH3:25])=[O:39])[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 100818122,4,6-Trimethoxyphenyl isocyanateHCID 105923395-Benzyl-3-dodecylisoxazole

Product 1

HCID 100758622-(3-Dodecyl-isoxazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418339ButyllithiumSolvent

Procedure

A stirred room temperature solution of 3-dodecyl-5-(phenylmethyl)isoxazole (38.3 g, 0.117 mol) in tetrahydrofuran (600 mL) was cooled to -78° C. under nitrogen. To the resulting precipitate was added dropwise a 2.01M solution (58 mL, 0.12 mol) in n-butyl lithium in hexanes over 10 minutes. The mixture was stirred for 1.25 hours before a solution of 2,4,6-trimethoxyphenyl isocyanate (24.43 g, 0.1168 mol) in tetrahydrofuran (350 mL) was added dropwise over 30 minutes. The mixture was stirred for 45 minutes then quenched with a dropwise addition of 1M HCl (235 mL, 0.235 mol) followed by ether (500 mL). The mixture was allowed to warm to room temperature. The organic layer was washed with 0.2M HCl , water, saturated sodium bicarbonate, and saturated sodium chloride, dried (MgSO4), and rotoevaporated to a solid. The material was recrystallized twice from diisopropyl ether and chromatographed on silica gel (830 g, 230- 400 mesh) using petroleum ether-ethyl acetate (2:1, 20×900 mL) to give a white solid; yield 40.7 g (65%), mp 106°-107° C.

Workup

  1. additionwas added dropwise over 30 minutes
  2. washThe organic layer was washed with 0.2M HCl , water, saturated sodium bicarbonate, and saturated sodium chloride
  3. dry with materialdried (MgSO4)
  4. customThe material was recrystallized twice from diisopropyl ether
  5. customchromatographed on silica gel (830 g, 230- 400 mesh)
  6. customto give a white solid

Sources & evidence

ORD record
ord-1a3af68a884b40c2b2c47a4207b41306
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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