Water → HCID 86697164, compound

HRID 237503Notes

Reaction equation

HRID 237503 reaction equation
[N:1]12[CH2:6][CH:5]1[CH2:4][CH2:3][S:2]2(=[O:8])=[O:7].[Br:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([OH:17])=[CH:12][C:11]=1[CH3:18].[H-].[Na+].O>CN(C)C(=O)C>[Br:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH:5]2[CH2:4][CH2:3][S:2](=[O:8])(=[O:7])[NH:1][CH2:6]2)=[CH:12][C:11]=1[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 819704-Bromo-3,5-dimethylphenolHCID 11320954HCID 11320954, compound

Product 1

HCID 86697164HCID 86697164, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

2-Thia-1-aza-bicyclo[3.1.0]hexane 2,2-dioxide (Liang, Jiang-Lin et al., Organic Letters, 2002, vol. 4, #25 p. 4507-4510) (300 mg) is added to a suspension of 4-bromo-3,5-dimethylphenol (1.14 g) and sodium hydride (140 mg of a 60% mineral oil suspension) in 25 mL of N,N-dimethylacetamide. The reaction mixture is stirred at 130° C. for 5 h. Water is added and the reaction mixture is extracted with ethyl acetate. The organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→30:70) to give the title compound. Yield: 220 mg.

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→30:70)

Sources & evidence

ORD record
ord-b41520d52b054581b015a9d18235363e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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