Acetonitrile → HCID 135611167, compound

HRID 1015422Notes

Reaction equation

HRID 1015422 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:18]1[NH:22][C:21](=[O:23])[O:20][N:19]=1.[F:24][C:25]1[CH:26]=[C:27]([N:32]=[C:33]=[O:34])[CH:28]=[C:29]([F:31])[CH:30]=1.C(#N)C>C1(C)C=CC=CC=1>[F:24][C:25]1[CH:26]=[C:27]([NH:32][C:33]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=3)=[CH:4][C:3]=2[C:18]2[NH:22][C:21](=[O:23])[O:20][N:19]=2)=[O:34])[CH:28]=[C:29]([F:31])[CH:30]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 27792821,3-Difluoro-5-isocyanatobenzene3×HCID 136075215HCID 136075215, compound

Product 1

HCID 135611167HCID 135611167, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 100 ml of dry toluene was 5 g of 3-(4-amino-4′-trifluoromethyl-biphenyl-3-yl)-4H-[1,2,4]oxadiazol-5-one suspended and 2.5 g of 3,5-difluorophenyl isocyanate was added, the reaction mixture was stirred at room temperature overnight, 1.3 g of 3,5-difluorophenyl isocyanate was added and stirring was continued overnight. 3,5-Difluorophenyl isocyanate (1.3 g) and 100 ml of acetonitrile was added, the reaction mixture was stirred at room temperature for 90 min. and evaporated to dryness. The residue was dissolved in 100 ml of boiling acetone, then cooled to 0° C. and filtrated. The precipitate was recrystallized from 200 ml of ethanol, after filtration while hot, the solution was added 400 ml of water. The product was isolated by filtration. Yield 4 g (54%) mp.>150° C. decomp.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. stirringthe reaction mixture was stirred at room temperature for 90 min.
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in 100 ml of boiling acetone
  6. temperaturecooled to 0° C.
  7. filtrationfiltrated
  8. customThe precipitate was recrystallized from 200 ml of ethanol
  9. filtrationafter filtration while hot, the solution
  10. additionwas added 400 ml of water
  11. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-ea4b952fa442446cb9da3fcd38140bcf
Source dataset
uspto-grants-2011_07
Patent number
US07985761B2

Reaction notes

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