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

HRID 1073127Notes

Reaction equation

HRID 1073127 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) cf 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-19adad2b321947e9a7736fb7b3198db3
Source dataset
uspto-grants-1990_11
Patent number
US04968679

Reaction notes

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