Triethylamine → HCID 19769927, compound

HRID 1590213Notes

Reaction equation

HRID 1590213 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[C:4]=1C(O)=O.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]1[O:48][C:47]2[C:42](=[C:43]([CH:49]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:50][NH2:51])[CH:44]=[CH:45][CH:46]=2)[O:41]1>C1(C)C=CC=CC=1>[CH2:40]1[O:48][C:47]2[C:42](=[C:43]([CH:49]([CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:50][NH:51][C:21]([NH:18][C:4]3[C:8]([O:14][CH3:15])=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:3]=3[O:2][CH3:1])=[O:30])[CH:44]=[CH:45][CH:46]=2)[O:41]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 684412,4,6-Trimethoxybenzoic acidHCID 199401P,P-Diphenylphosphinic azideHCID 10444090HCID 10444090, compound

Product 1

HCID 19769927HCID 19769927, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

To 430 mg (2.0 mmol) of 2,4,6-trimethoxybenzoic acid, were added 10 ml of toluene, 0.52 ml (3.38 mmol) of triethylamine and 0.73 ml (3.40 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 520 mg (2.2 mmol) of 2-(2,3-methylenedioxyphenyl)heptylamine was added and the mixture was stirred at room temperature over night. The reaction mixture was subjected to purification by silica-gel column chromatography and recrystallization from a mixed solvent of hexane and ethyl acetate to obtain 360 mg of 1-(2-(2,3-methylenedioxyphenyl)heptyl)-3-(2,4,6-trimethoxyphenyl)urea (Yield: 42.1%).

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature over night
  4. customThe reaction mixture was subjected to purification by silica-gel column chromatography and recrystallization from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-61b91799d3d041ddabd1f32b13d9313d
Source dataset
uspto-grants-1993_04
Patent number
US05202351

Reaction notes

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