HCID 13853371, compound → HCID 59199389, compound

HRID 2089543Notes

Reaction equation

HRID 2089543 reaction equation
S1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:3][CH2:2]1.O[O:17][S:18]([O-:20])=O.[K+]>CO.O>[O:17]=[S:18]1(=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 13853371HCID 13853371, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 59199389HCID 59199389, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-thiochroman-4-yl-1H-imidazole, which can be prepared as described in Example 16, (130 mg, 0.60 mmol) in methanol (3 mL) at 0° C. is added dropwise a solution of Oxone® (excess) in water (3 mL). The reaction mixture is stirred overnight at room temperature. The reaction is then concentrated an the resulting residue is purified by silica gel flash chromatography (0:1 to 1:19 methanol-dichloromethane), to afford 1-(1,1-dioxo-thiochroman-4-yl)-1H-imidazole; MS: (ESI) m/z 249.1 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 2.83-3.13 (m, 2 H), 3.42-3.65 (m, 1 H), 3.64-3.82 (m, 1 H), 6.18 (t, J=7.1 Hz, 1 H), 7.14 (d, J=7.6 Hz, 1 H), 7.49-7.78 (m, 4 H), 8.02 (d, J=8.0 Hz, 1 H), 9.06 (s, 1 H).

Workup

  1. concentrationThe reaction is then concentrated an the resulting residue
  2. customis purified by silica gel flash chromatography (0:1 to 1:19 methanol-dichloromethane)

Sources & evidence

ORD record
ord-72c40cae593546c4ac24f18b1b68f231
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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