Hydrogen Bromide → HCID 178503118, compound

HRID 891297Notes

Reaction equation

HRID 891297 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][N:4]1[C:9](=[O:10])[C:8]([O:11]C)=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[CH:6]=[N:5]1.Br.O>C(O)(=O)C>[F:22][C:2]([F:1])([F:21])[CH2:3][N:4]1[C:9](=[O:10])[C:8]([OH:11])=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[CH:6]=[N:5]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 21934128HCID 21934128, compound

Product 1

HCID 178503118HCID 178503118, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(2,2,2-Trifluoroethyl)-4-methoxy-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone (2 g, 6.1 mmol) and hydrobromic acid (40% in water, 20 mL) in acetic acid (40 mL) was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and water (50 mL) was added. The crystals formed were filtered, washed with water and 5% ethyl acetate in hexanes, and dried to constant weight. The product was obtained as a white solid (yield: 1.75 g, 91%). 1H NMR (300 MHz, CDCl3) δ 2.54 (s, 3H), 4.82 (q, J=9 Hz, 2H), 7.47 (d, J=9 Hz, 2H), 7.65 (d, J=9 Hz, 2H), 7.73 (br s, 1H), 8.00 (s, 1H). MS (DCI) m/z 317 (M+H)+.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe crystals formed
  3. filtrationwere filtered
  4. washwashed with water and 5% ethyl acetate in hexanes
  5. customdried to constant weight

Sources & evidence

ORD record
ord-dff0f860e7ea45db88936946e901a76f
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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