Triethylamine → (R)-1-[2-(2, 3-methylenedioxyphenyl) heptyl]-3-(2, 3-dihydro-2, 2-dimethylbenzofuran-7-yl) urea

HRID 1756780Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10](C(O)=O)[C:4]=2[O:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.C([N:34]([CH2:37]C)CC)C.[CH2:39]1[O:47][C:46]2[C:41](=[C:42]([C@@H:48]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:49][NH2:50])[CH:43]=[CH:44][CH:45]=2)[O:40]1>C1(C)C=CC=CC=1.CCCCCC>[CH2:39]1[O:47][C:46]2[C:41](=[C:42]([C@@H:48]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:49][NH:50][C:37]([NH:34][C:10]3[C:4]4[O:3][C:2]([CH3:1])([CH3:14])[CH2:6][C:5]=4[CH:7]=[CH:8][CH:9]=3)=[O:22])[CH:43]=[CH:44][CH:45]=2)[O:40]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 0.90 g of 2, 3-dihydro-2, 2-dimethylbenzofuran-7-carboxylic acid, 1.38 g of diphenylphosphoryl azide, 0.61 g of triethylamine and 12 ml of toluene was stirred at 90° C. for 2 hours and allowed to cool with ice. To this mixture was added a solution of 1.18 g of (R)-2-(2, 3-methylenedioxyphenyl) heptylamine in 10 ml of toluene under ice cooling and stirring, and the resultant mixture was stirred at room temperature for 2 hours and mixed with 30 ml of n-hexane. The precipitated crystals were filtered and recrystallized from ethyl acetate to give 1.02 g of the titled compound.

Workup

temperatureto cool with ice
stirringstirring
filtrationThe precipitated crystals were filtered
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-5b424b4ba655484d9da92d7986673b0f
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05442060

Reaction notes

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