2-Bromopropane → HCID 86754228, compound

HRID 581908Notes

Reaction equation

HRID 581908 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:7]1[CH:27]=[CH:26][C:10]2[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:15]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1)[CH3:6])[CH3:2].[H-].[Na+].Br[CH:31](C)C>CN(C=O)C.O>[CH:1]([O:3][N:4]=[C:5]([C:7]1[CH:27]=[CH:26][C:10]2[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:15]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1)[CH3:6])([CH3:31])[CH3:2]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 73769685HCID 73769685, compound

Product 1

HCID 86754228HCID 86754228, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of 33i (Example 14) (0.4 g, 1.22 mmol) in dry DMF (5 ml) is added sodium hydride (50 mg of a 60% dispersion in mineral oil). The mixture is stirred at 30-40° C. for 30 min. 2-Bromopropane (0.14 ml, 1.49 mmol) is added and the mixture is stirred at 40° C. over night. After cooling the mixture is diluted with 4 volumes of water and extracted with dichloromethane. The organic extract is concentrated and eluted through silica gel with ethyl acetate to yield 0.15 g 33j (33%). Mp 77-80° C.

Workup

  1. stirringthe mixture is stirred at 40° C. over night
  2. temperatureAfter cooling the mixture
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. concentrationis concentrated
  6. washeluted through silica gel with ethyl acetate

Sources & evidence

ORD record
ord-65b43a1d00ce4759946df403061411bf
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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