Water → HCID 22921534, compound

HRID 2258624Notes

Reaction equation

HRID 2258624 reaction equation
[CH3:1][N:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:6](=[O:7])[N:5]([C:14]2[CH:26]=[CH:25][C:17]3[N:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[NH:20][C:16]=3[CH:15]=2)[C:3]1=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH:35]=[CH2:36].O>CN(C)C=O>[CH3:1][N:2]1[C:9]([C:10]([F:11])([F:12])[F:13])=[CH:8][C:6](=[O:7])[N:5]([C:14]2[CH:26]=[CH:25][C:17]3[N:18]=[C:19]([C:21]([F:23])([F:24])[F:22])[N:20]([CH2:36][CH:35]=[CH2:34])[C:16]=3[CH:15]=2)[C:3]1=[O:4]

Participants

7

Reactant 5

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 22921542HCID 22921542, compoundHCID 178480548HCID 178480548, compound

Product 1

HCID 22921534HCID 22921534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, 1.3 grams (0.003 mole) of a tautomeric mixture of 1-methyl-3-(2-trifluoromethylbenzimidazol-5-yl)-6-trifluoromethyluracil and 1-methyl-3-(2-trifluoromethylbenzimidazol-6-yl)-6-trifluoromethyluracil (prepared in Example 4) in 15 mL of N,N-dimethylformamide was stirred, and 0.9 gram (0.007 mole) of potassium carbonate was added. The reaction mixture was then stirred at ambient temperature for one hour, and 0.5 gram (0.004 mole) of 3-bromopropene was added in one portion. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for an additional two hours. The reaction mixture was then poured into water, and the resultant solid precipitate was collected by filtration. The solid was washed with water and then with diethyl ether. Thin layer chromatographic analysis of the solid indicated it to be a 1:1 mixture of the proposed products. The solid was subjected to high pressure liquid chromatography, with 5% 1-methylethanol in hexane as the eluant. The appropriate product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of 1-methyl-3-[1-(2-propen-1-yl)-2-trifluoromethylbenzimidazol-6-yl]-6-trifluoromethyluracil, mp 171°-173° C. (compound 9). Other appropriate product-containing fractions were combined and concentrated under reduced pressure, yielding 0.4 gram of 1-methyl-3-[1-(2-propen-1-yl)-2-trifluoromethylbenzimidazol-5-yl]-6-trifluoromethyluracil, mp 185°-187° C. The NMR spectra were consistent with the proposed structures.

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction mixture was stirred at ambient temperature for an additional two hours
  3. filtrationthe resultant solid precipitate was collected by filtration
  4. washThe solid was washed with water
  5. additiona 1:1 mixture of the proposed products
  6. additionThe appropriate product-containing fractions
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c681b36c70804c30b3579b6dbe95f1e7
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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