Benzyl mercaptan → HCID 118094025, compound

HRID 515540Notes

Reaction equation

HRID 515540 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:10]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]2[C:11]=1[N:12]=[CH:13][CH:14]=[N:15]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([S:8][C:10]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]2[C:11]=1[N:12]=[CH:13][CH:14]=[N:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 532168595-Bromo-7-chloroquinoxaline

Product 1

HCID 118094025HCID 118094025, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl mercaptan (0.51 g, 4.1 mmol) was added dropwise to a mixture of 5-bromo-7-chloroquinoxaline (1 g, 4.1 mmol), cesium carbonate (1.6 g, 4.92 mmol) at 0° C. in DMF (25 ml) under nitrogen. The reaction mixture was allowed to warm to room temperature, stirred for 2 hours and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried with sodium sulfate and concentrated. Purification by column chromatography gave 5-(benzylthio)-7-chloroquinoxaline (rf=0.39 in 9:1 hexanes/ethyl acetate) as a yellow solid. The undesired regioisomer elutes afterwards (rf=0.27 in 9:1 hexanes/ethyl acetate).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-6a1da87537914696860585a07f579032
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

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