Hydrogen Peroxide → HCID 22615167, compound

HRID 1457832Notes

Reaction equation

HRID 1457832 reaction equation
[F:1][C:2]1[C:3]([CH:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=2)=S)[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH:21]O>C(O)(=O)C>[F:1][C:2]1[C:3]([CH:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=2)=[O:21])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 22100983HCID 22100983, compound

Product 1

HCID 22615167HCID 22615167, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 400 mg (1.13 mmole) of N-(3-fluoropyrid-2-yl)eth-2-yl-N'-(5-bromopyrid-2-yl)-thiourea (see Example 920 of W093/03022) in 11.5 ml of glacial acetic acid was treated with 0.8 ml (7.83 mmole) of 30% hydrogen peroxide. After stirring 1.5 hrs at room temperature, the solution was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate (1×). The organic layer was back washed with brine (1×) and dried over sodium sulfate. Purification by flash silica gel chromatography (50% ethyl acetate/hexanes) gave 75 mg (19.6%) of the titled compound as a white solid: mp 151°-154° C.; IR (KBr, cm-1) 3200, 3100, 3000, 1685, 1557, 1467, 1360, 1290, 1230, 839; 1H NMR (300 MHz, DMSO-d6) δ 9.30 (br. s., 1H), 8.40 (d, 1H), 8.22 (d, 1h), 7.85 (dd, 1H), 7.79 (br.t., 1H), 7.70 (dt, 1H), 7.45 (d, 1H), 7.30-7.40 (m, 1H), 3.58 (q, 2H), 3.00 (t, 2); MS (FD) m/e 340 (Mt). Anal. Calc'd. for C13H12BrFN4O: C, 46.04; H, 3.57; N, 16.52. Found: C, 46.25; H, 3.66; N, 16.54.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate (1×)
  3. washThe organic layer was back washed with brine (1×)
  4. dry with materialdried over sodium sulfate
  5. customPurification by flash silica gel chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-223abbab66924f14ac4ad814027d3c96
Source dataset
uspto-grants-1998_12
Patent number
US05849769

Reaction notes

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