1,3-Dimethyl-2-imidazolidinone → HCID 54234545, compound

HRID 1037701Notes

Reaction equation

HRID 1037701 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(C1C=CC=C(C(C)(C)C)C=1[O-])(C)(C)C.[Na+].CN1CCN(C)C1=O.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>Cl.O1CCCC1>[CH3:42][S:43]([O:15][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][C:7]=1[C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:45])=[O:44]

Participants

8

Reactant 5

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 314052,6-Di-tert-butylphenolHCID 23662146HCID 23662146, compound

Product 1

HCID 54234545HCID 54234545, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

50 mL of a tetrahydrofuran (THF) solution containing 10.00 g (0.049 mol) of 2,6-di-tert-butylphenol were dropped into 100 mL of a THF suspension of 2.03 g (0.051 mol) of 60% oil-dispersed sodium hydride at 0° C. followed by stirring for 1 hour at the same temperature to prepare sodium 2,6-di-tertbutylphenoxide. 5.81 g (0.051 mol) of 1,3-dimethyl-2-imidazolidinone were added to this solution, and after stirring for 30 minutes at 0° C., 5.83 g (0.051 mol) of methanesulfonyl chloride were dropped in followed by stirring for 2 hours at 25° C. The reaction liquid was placed in 30% aqueous hydrochloric acid solution and following separation of the organic layer, the organic layer was washed once with 1 N aqueous NaOH solution and twice with water followed by drying with MgSO4 and concentrating. The resulting crude crystals were purified by crystallization with a 1/1 (volumetric ratio) mixture of n-hexane and isopropanol to obtain 4.8 g (yield: 35%) of 2,6-di-tert-butylphenyl methanesulfonate (white crystals, melting point: 83° C.).

Workup

  1. stirringafter stirring for 30 minutes at 0° C.
  2. stirringby stirring for 2 hours at 25° C
  3. customThe reaction liquid
  4. customseparation of the organic layer
  5. washthe organic layer was washed once with 1 N aqueous NaOH solution and twice with water
  6. dry with materialby drying with MgSO4
  7. concentrationconcentrating
  8. customThe resulting crude crystals were purified by crystallization with a 1/1 (volumetric ratio) mixture of n-hexane and isopropanol

Sources & evidence

ORD record
ord-fe538270eadd44f780d7bdabe9ccfbef
Source dataset
uspto-grants-2013_10
Patent number
US08546599B2

Reaction notes

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