2-Bromopropane → HCID 14473648, compound

HRID 1646256Notes

Reaction equation

HRID 1646256 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[CH:18](Br)([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH:18]([CH3:20])[CH3:19])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 63582-Bromopropane2×HCID 11430Potassium Carbonate2×HCID 14473647HCID 14473647, compound

Product 1

HCID 14473648HCID 14473648, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 696 mg of the compound prepared in Example 11, 405 mg of isopropyl bromide and 248 mg of potassium carbonate in 15 ml of anhydrous dimethylformamide is heated under nitrogen for one hour to 100° C. With incomplete reaction, equivalent amounts of isopropyl bromide and potassium carbonate are furthermore added two to three times. For working up purposes, the solvent is distilled off and the remaining residue is stirred with water. The thus-obtained crude product is filtered off, dried, and purified by chromatography on silica gel with toluene/ethyl acetate (8:2), thus producing 782 mg (95%) of the title compound as a slightly yellow oil.

Workup

  1. temperatureis heated under nitrogen for one hour to 100° C
  2. additionare furthermore added two to three times
  3. distillationthe solvent is distilled off
  4. customThe thus-obtained crude product
  5. filtrationis filtered off
  6. customdried
  7. custompurified by chromatography on silica gel with toluene/ethyl acetate (8:2)

Sources & evidence

ORD record
ord-cf80256b127b4526b8c2f04b087fc2a7
Source dataset
uspto-grants-1993_01
Patent number
US05179111

Reaction notes

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