Diethylcarbamoyl chloride → 2-Dipropylamino-8-[2-(3,3-diethylureido)-ethoxy]-1,2,3,4-tetrahydronaphthalene

HRID 728083Notes

Reaction equation

HRID 728083 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH2:16][CH2:17][NH2:18])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:28]([N:30]([CH2:34][CH3:35])[C:31](Cl)=[O:32])[CH3:29].C(OC(C)C)(C)C.C(O)C>C1(C)C=CC=CC=1>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH2:16][CH2:17][NH:18][C:31]([N:30]([CH2:34][CH3:35])[CH2:28][CH3:29])=[O:32])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 141812122-Dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthaleneHCID 23358034Diisopropyl ether ethanol

Product 1

HCID 198234942-Dipropylamino-8-[2-(3,3-diethylureido)-ethoxy]-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.45 g (5 mmol) of 2-dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthalene and 1.38 g (10 mmol) of potassium carbonate were initially introduced into 20 ml of toluene. 0.77 g (5.5 mmol) of diethylcarbamoyl chloride was then added dropwise, and the mixture was stirred for 2 h at +100° C. The mixture was then filtered and evaporated. The product was obtained by chromatography over silica gel 60, 40-63 μm, using diisopropyl ether/ethanol, 3:2.

Workup

  1. filtrationThe mixture was then filtered
  2. customevaporated
  3. customThe product was obtained by chromatography over silica gel 60, 40-63 μm

Sources & evidence

ORD record
ord-37bdbc1a72ea47f194ac825ed86f2b5f
Source dataset
uspto-grants-1991_09
Patent number
US05047422

Reaction notes

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