Triethylamine → HCID 19769917, compound

HRID 1590214Notes

Reaction equation

[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([CH:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])C(O)=O)[CH:5]=[CH:6][CH:7]=2)[O:2]1.C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[CH:43]([C:46]1[CH:52]=[CH:51][CH:50]=[C:49]([CH:53]([CH3:55])[CH3:54])[C:47]=1[NH2:48])([CH3:45])[CH3:44]>C1(C)C=CC=CC=1>[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([CH:10]([NH:21][C:24]([NH:48][C:47]3[C:46]([CH:43]([CH3:45])[CH3:44])=[CH:52][CH:51]=[CH:50][C:49]=3[CH:53]([CH3:55])[CH3:54])=[O:33])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:5]=[CH:6][CH:7]=2)[O:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

To 800 mg (3.20 mmol) of 2-(2,3-methylenedioxyphenyl)heptanoic acid, were added 10 ml of toluene, 0.59 ml (3.84 mmol) of triethylamine and 1.0 ml (4.8 mmol) of diphenylphosphoryl azide, and the mixture was stirred at 100° C. for one hour. After cooling the mixture to room temperature, 5 ml of a toluene solution containing 570 mg (3.20 mmol) of 2,6-diisopropylaniline was added and the mixture was stirred at room temperature over night. The reaction mixture was subjected to purification by silica-gel column chromatography (eluent: hexane/ethyl acetate=5/1) and recrystallization from a mixed solvent of hexane and ethyl acetate to obtain 510 mg of 1-(1-(2,3-methylenedioxyphenyl)hexyl)-3-(2,6-diisopropylphenyl)urea (Yield: 38%).

Workup

temperatureAfter cooling the mixture to room temperature
additionwas added
stirringthe mixture was stirred at room temperature over night
customThe reaction mixture was subjected to purification by silica-gel column chromatography (eluent: hexane/ethyl acetate=5/1) and recrystallization from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record: ord-1bb48db513684fce894999c6a9064fd9
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05202351

Reaction notes

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