Potassium Bromide → HCID 21997636, compound

HRID 1977108Notes

Reaction equation

HRID 1977108 reaction equation
[C:1]([CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[NH:15][C:16](=[O:18])[CH3:17])#[N:2].I([O-])(=O)(=O)=[O:20].[Na+].[K+].[Br-]>O1CCOCC1.O>[C:1]([CH2:3][S:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:14])[F:13])=[CH:7][C:6]=1[NH:15][C:16](=[O:18])[CH3:17])=[O:20])#[N:2]

Participants

6

Reactant 3

HCID 253877Potassium BromideHCID 21997631HCID 21997631, compoundHCID 23667635Sodium periodate

Product 1

HCID 21997636HCID 21997636, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
40 °C

Procedure

A solution of N-(2-cyanomethylsulfanyl-5-trifluoromethylphenyl)acetamide(0.42 g) in dioxane (2.50 ml) was added dropwise to a stirred solution of sodium periodate (0.69 g) in a mixture of water (6 ml) and dioxane (1.50 ml) at ambient temperature. An additional amount of dioxane (2.50 ml) was added. The mixture was stirred at 40° C. for 6½ h, then at room temperature overnight. A precipitate was removed by filtration and washed on the filter with dichlorometane (20 ml). The two phases of the filtrate were shaken and separated. The aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The more polar component of the residue was isolated by flash chromatography on silica gel eluted with 1) ether and 2) ethyl acetate to give a slowly crystallizing oil. Trituration with petroleum ether and subsequent drying gave white crystals. Yield 0.16 g (38%); mp 149-151° C.; 1H-NMR(CDCl3) δ (ppm): 9.9 (br, 1H), 8.70 (d, J=2 Hz, 1H), 7.68-7.46 (d+dd, J=8Hz and 8 Hz/2 Hz, 1H+1H), ABX-system at 4.13 (d, J=16 Hz, 1H) and 3.98 (d, J=16 Hz, 1H), 2.25 (s, 3H); 13C-NMR (DMSO-d6) δ (ppm): 170.1, 141.3, 135.8, 132.7 (q, J=32 Hz), 127.0, 123.5 (CF3, J=273 Hz), 123.1 (J=3.6 Hz), 122.0 (J=3.6 Hz), 113.3 (C≡N), 42.6 (CH2), 23.2 (CH3); IR (KBr) ν (cm−1): 3220 (NH), 2252 (C≡N), 1691 (C═O), 1532, 1476, 1337, 1273, 1176, 1128, 1033, 888, 675.

Workup

  1. customat room temperature
  2. customovernight
  3. customA precipitate was removed by filtration
  4. washwashed on the
  5. filtrationfilter with dichlorometane (20 ml)
  6. stirringThe two phases of the filtrate were shaken
  7. customseparated
  8. extractionThe aqueous phase was extracted with dichloromethane (2×10 ml)
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe more polar component of the residue was isolated by flash chromatography on silica gel
  13. washeluted with 1) ether and 2) ethyl acetate
  14. customto give
  15. customa slowly crystallizing oil
  16. dry with materialTrituration with petroleum ether and subsequent drying
  17. customgave white crystals

Sources & evidence

ORD record
ord-ac3d8d4441454a1e8e1fbc9ae4bdd1f7
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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