Water → HCID 131728513, compound

HRID 1172548Notes

Reaction equation

HRID 1172548 reaction equation
[CH3:1]I.[OH-].[Na+].C[O:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[CH2:15][S:14](=[O:24])(=[O:23])[C:13]=2[CH:25]=1)=[O:8].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH3:1][N:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH2:15][S:14](=[O:24])(=[O:23])[C:13]2[CH:25]=[C:9]([C:7]([OH:6])=[O:8])[CH:10]=[CH:11][C:12]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 131728514HCID 131728514, compound

Product 1

HCID 131728513HCID 131728513, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

Methyl iodide (0.03 ml, 0.49 mmol), tetrabutylammonium hydrogen sulphate (0.112 g, 0.33 mmol) and 50% aqueous sodium hydroxide (0.5 mL) were added to a solution of Example 166e (0.1 g, 0.33 mmol) in benzene (2 mL). The reaction mixture was stirred for 7 h at room temperature, treated with water and extracted with ethyl acetate. The organic extract was washed with water, 10% aqueous HCl, dried, concentrated and subjected to hydrolysis as described in Example 1i to obtain the title compound. (Synthesis 124, (1976)). Yield: 8.80%; 1H NMR (DMSO-d6): δ 3.50 (s, 3H, CH3), 5.00 (s, 2H, CH2), 7.30-7.60 (m, 5H, Ar), 8.01 (d, 1H, Ar), 8.20 (s, 1H, Ar); MS: m/e (ES+) 304 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water, 10% aqueous HCl
  4. customdried
  5. concentrationconcentrated
  6. customsubjected to hydrolysis

Sources & evidence

ORD record
ord-71b08749efb1469894d38c39d212cda8
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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