Acetic Acid → HCID 68305187, compound

HRID 1842597Notes

Reaction equation

HRID 1842597 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[CH:5][NH:4][N:3]=1.CN(/[CH:11]=[C:12](/[C:17]([F:20])([F:19])[F:18])\[CH:13]=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)(=O)C>C(O)C>[Br:7][C:6]1[CH:5]=[N:4][N:3]2[CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=[N:1][C:2]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 15877725[(2E)-3-(dimethylamino)-2-(trifluoromethyl)prop-2-en-1-ylidene]dimethylazanium; hexafluoro-lambda5-phosphanuideHCID 178509245HCID 178509245, compound

Product 1

HCID 68305187HCID 68305187, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-4-bromopyrazole (4.29, 26.5 mmol) and 2-(trifluoromethyl)-1,3-bis(dimethylamino)trimethinium hexafluorophosphate (9.00 g, 26.5 mmol) were dissolved in ethanol (52.9 mL) and acetic acid (35.3 mL) and the reaction heated to 70° C. for 16 h. The solution was cooled to room temperature and concentrated. The residue was filtered through a fritted funnel, the precipitate washed with water, and dried under reduced pressure to afford the title compound (6.22 g, 23.4 mmol). LRMS (APCI) calc'd for (C7H3BrF3N3) [M+H]+, 266.0; found 265.9. 1H NMR (CDCl3, 500 MHz) δ 8.96 (d, J=1.1, 2.1, 1H), 8.71 (d, J=2.1, 1H), 8.28 (s, 1H).

Workup

  1. concentrationconcentrated
  2. filtrationThe residue was filtered through a fritted funnel
  3. washthe precipitate washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b76cec3d45704f3d82822b5103fdff59
Source dataset
uspto-grants-2015_02
Patent number
US08946237B2

Reaction notes

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