Triethylamine → HCID 19769912, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1C(O)=O.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[CH2:38]1[O:46][C:45]2[CH:44]=[CH:43][C:42]([CH:47]([CH2:50][CH2:51][CH2:52][CH3:53])[CH2:48][NH2:49])=[CH:41][C:40]=2[O:39]1>C1(C)C=CC=CC=1>[CH2:38]1[O:46][C:45]2[CH:44]=[CH:43][C:42]([CH:47]([CH2:50][CH2:51][CH2:52][CH3:53])[CH2:48][NH:49][C:19]([NH:16][C:4]3[C:8]([O:12][CH3:13])=[CH:9][CH:10]=[CH:11][C:3]=3[O:2][CH3:1])=[O:28])=[CH:41][C:40]=2[O:39]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To 1 g (6.41 mmol) of 2,6-dimethoxybenzoic acid, were added 10 ml of toluene, 1.05 ml (6.79 mmol) of triethylamine and 1.41 ml (6.54 mmol) of diphenylphosphoryl azide and stirred at 100° C. for one hour. The reaction solution was cooled to room temperature, then added with a 5 ml of toluene solution of 1.40 g (6.41 mmol) of 2-(3,4-methylenedioxyphenyl)-hexylamine and stirred overnight at room temperature. The thus treated reaction solution was purified by silica gel column chromatography (developed with a 2/1 mixture of hexane and ethyl acetate) and then recrystallized from the hexane/ethyl acetate mixed solvent to obtain 330 mg of 1-(2-(3,4-methylenedioxyphenyl)hexyl)-3-(2,6-dimethyoxyphenyl)urea (yield: 12.9%).
Workup
- temperatureThe reaction solution was cooled to room temperature
- stirringstirred overnight at room temperature
- customThe thus treated reaction solution
- customwas purified by silica gel column chromatography (
- additiondeveloped with a 2/1 mixture of hexane and ethyl acetate) and
- customthen recrystallized from the hexane/ethyl acetate mixed solvent
Sources & evidence
- ORD record
- ord-b2cf3e30e73044a1b8a85389824bc4cc
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05202351
Reaction notes
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