Dimethylformamide → HCID 11036020, compound

HRID 479297Notes

Reaction equation

HRID 479297 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([CH:9]([CH3:11])[CH3:10])[N:3]=1.Cl.[F:13][C:14]([F:28])([F:27])[C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)[O:18][CH2:19][CH:20]([NH2:23])[CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[NH2:1][C:2]1[N:3]=[C:4]([CH:9]([CH3:11])[CH3:10])[N:5]=[C:6]([NH:23][CH:20]([CH2:21][CH3:22])[CH2:19][O:18][C:17]2[CH:24]=[CH:25][CH:26]=[C:15]([C:14]([F:13])([F:27])[F:28])[CH:16]=2)[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 111165324-Chloro-6-isopropyl-1,3,5-triazin-2-amineHCID 18769949HCID 18769949, compound

Product 1

HCID 11036020HCID 11036020, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2.6 g (0.015 mol) of 2-amino4-chloro-6-isopropyl-1,3,5-triazine, 4.0 g (0.015 mol) of 1-(3-trifluoromethylphenoxy)-2-aminobutane hydrochloride and 6.2 g (0.045 mol) of potassium carbonate were added to 50 ml of dimethylformamide (DMF). The mixture was heated at 80° C. for 3 hours, added into water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and filtered and the solvent was evaporated under reduced pressure. Purification by silica gel column chromatography using ethyl acetate/petroleum ether (1:1) gave 4.2 g (76%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-df084aa5d5b84d14abbaf903b7ab6921
Source dataset
uspto-grants-2003_11
Patent number
US06645916B1

Reaction notes

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