Methanol → 8-iodo-3-(3-(methylsulfonyl)propyl)quinazoline-2,4(1H,3H)-dione

HRID 1056415Notes

Reaction equation

HRID 1056415 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][CH2:15]SC)[C:7]2=[O:18].O[O:20][S:21]([O-:23])=O.[K+].[CH3:25]O>O>[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][CH2:15][S:21]([CH3:25])(=[O:23])=[O:20])[C:7]2=[O:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 897844618-iodo-3-(3-(methylthio)propyl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 897837608-iodo-3-(3-(methylsulfonyl)propyl)quinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 150 mL round-bottomed flask was added 8-iodo-3-(3-(methylthio)propyl)quinazoline-2,4(1H,3H)-dione (1.34 g, 3.56 mmol) in MeOH (15 mL) and oxone monopersulfate (3.28 g, 5.34 mmol, Sigma Aldrich) in water (15 mL) was added. The mixture was stirred at RT for 24 h. Another 0.5 equiv. of oxone was added and the mixture was stirred at 35° C. for 24 h. The mixture was diluted with water (30 mL) and extracted with DCM (60 mL×3). The combined organic layers were dried (MgSO4), filtered and concentrated to give the crude product (1.09 g). MS (ESI, pos. ion) m/z: 408.8 (M+1).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 35° C. for 24 h
  3. extractionextracted with DCM (60 mL×3)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d2ceaa80fa1e45108a49f66d46db423b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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