Sodium hydride → HCID 86703887, compound

HRID 471452Notes

Reaction equation

HRID 471452 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[H-].[Na+].[O:13]=[S:14]1(=[O:26])[CH2:18][CH2:17][CH2:16][N:15]1[CH2:19][CH2:20]OS(C)(=O)=O>>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:20][CH2:19][N:15]2[CH2:16][CH2:17][CH2:18][S:14]2(=[O:26])=[O:13])=[CH:4][C:3]=1[CH3:10]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 819704-Bromo-3,5-dimethylphenolHCID 57794291HCID 57794291, compound

Product 1

HCID 86703887HCID 86703887, compound

Procedure

4-Bromo-3,5-dimethylphenol (1.25 g, 6.17 mmol) and sodium hydride (60% on mineral oil, 160 mg, 3.95 mmol) are suspended in dry N,N-dimethylacetate (25 mL) and stirred for 30 minutes at room temperature. Methanesulfonic acid 2-(1,1-dioxo-isothiazolidin-2-yl)-ethyl ester (Patent EP1479684 A1, 600 mg, 2.47 mmol;) is added and the mixture stirred at 80° C. for 5 hours. The mixture is concentrated under vacuum, diluted with water and extracted with ethyl acetate. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane) to give the title compound. (Yield: 350 mg).

Workup

  1. stirringthe mixture stirred at 80° C. for 5 hours
  2. concentrationThe mixture is concentrated under vacuum
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. customthe solvent removed
  7. customThe residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-5bfcdb716c8040d29c9fbf09b13a14b9
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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