Ethanethiol → HCID 70977846, compound

HRID 1521593Notes

Reaction equation

HRID 1521593 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].CS(O[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1)(=O)=O>CN(C)C=O>[Br:18][C:16]1[CH:15]=[N:14][CH:13]=[C:12]([CH2:11][S:5][CH2:3][CH3:4])[CH:17]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 57885697HCID 57885697, compound

Product 1

HCID 70977846HCID 70977846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cooled (0° C.) solution of sodium hydride (60% dispersion in mineral oil, 0.094 g, 2.35 mmol) in N,N-dimethylformamide (9.4 mL) was added ethanethiol (0.140 mL, 1.88 mmol). The reaction was warmed to room temperature and stirred for 30 minutes. It was then cooled to 0° C., and a solution of the title compound from Example 62 Step A (0.250 g, 0.939 mmol) in N,N-dimethylformamide (1 mL) added. The resulting solution stirred at room temperature until the reaction was complete. The reaction was then quenched with water and extracted with ethyl acetate. The combined organic extracts were washed with water and saturated aqueous sodium chloride solution, dried, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes) provided the title compound: LCMS m/z 233.91 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.50 (s, 1H), 8.39 (s, 1H), 7.79 (s, 1H), 3.62 (s, 2H), 2.39 (q, J=7.4, 2H), 1.19 (t, J=7.4, 3H).

Workup

  1. temperatureIt was then cooled to 0° C.
  2. stirringThe resulting solution stirred at room temperature until the reaction
  3. customThe reaction was then quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with water and saturated aqueous sodium chloride solution
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3facb623e2b44941aa8adeb881e56bed
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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