Diisopropyl Ether → 2-Dipropylamino-8-[2-(3-methylureido)ethoxy]1,2,3,4-tetrahydronaphthalene

HRID 728085Notes

Reaction equation

HRID 728085 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].[CH3:22][N:23]=[C:24]=[O:25].C(OC(C)C)(C)C>C(N(CC)CC)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:24]([NH:23][CH3:22])=[O:25])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 12228Methyl IsocyanateHCID 141812122-Dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 141812152-Dipropylamino-8-[2-(3-methylureido)ethoxy]1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent

Procedure

1.45 g (5 mmol) of 2-dipropylamino-8-(2-aminoethoxy)-1,2,3,4-tetrahydronaphthalene were initially introduced into 20 ml of toluene. The reaction was catalyzed using 3 drops of triethylamine, and 0.325 ml (5.5 mmol) of methyl isocyanate was then added dropwise. The mixture was stirred for 1 h at +25° C. The mixture was evaporated, and the residue obtained was stirred with hot diisopropyl ether. The mixture was cooled, and the product was filtered off under suction.

Workup

  1. additionwas then added dropwise
  2. customThe mixture was evaporated
  3. customthe residue obtained
  4. temperatureThe mixture was cooled
  5. filtrationthe product was filtered off under suction

Sources & evidence

ORD record
ord-72e8fcf43a844fef8d5270e5ba378efa
Source dataset
uspto-grants-1991_09
Patent number
US05047422

Reaction notes

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