Ethyl Bromide → HCID 22902344, compound

HRID 1489666Notes

Reaction equation

HRID 1489666 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:29](NCC)[CH3:30].C(Br)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][N:19]=2)[CH2:29][CH3:30])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 8021DiethylamineHCID 22902346HCID 22902346, compound

Product 1

HCID 22902344HCID 22902344, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2 g of 3-{3-[2-(3,4-dimethoxyphenyl)-ethylamino]-propyloxy}-5-phenyl-1,2,4-oxadiazole (for preparation, see Example 69) were dissolved in 20 ml dimethylformamide. 0.9 ml of diethylamine and 0.6 g ethyl bromide were added to the solution and the reaction mixture was heated at 50° C. for 3.5 hours. For workup, the reaction mixture was then concentrated to dryness and the residue dissolved in dichloromethane. A sufficient quantity of water was added to the solution for a clear phase separation to occur. The mixture was shaken and the organic phase separated out, dried with sodium sulfate, filtered, and concentrated. The crude oily title compound obtained was refined by medium-pressure chromatography on fine-grained silica gel using ethyl acetate/methanol/concentrated aqueous ammonia solution, ratio 9:1:0.05, as the eluent. 1.3 g of the title compound were obtained as a yellow oil.

Workup

  1. concentrationFor workup, the reaction mixture was then concentrated to dryness
  2. dissolutionthe residue dissolved in dichloromethane
  3. additionA sufficient quantity of water was added to the solution for a clear phase separation
  4. customthe organic phase separated out
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a5c3d8312d1a4c39940a5faaf35a8488
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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