Methanol → 4,4-Dimethyl-1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80272Notes

Reaction equation

HRID 80272 reaction equation
Cl[CH2:2][C:3]([NH:6][C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[O:8])([CH3:5])[CH3:4].[H-].[Na+].CO>C1COCC1.C(Cl)(Cl)Cl>[CH3:2][C:3]1([CH3:5])[CH2:4][N:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[CH3:16])[C:7](=[O:8])[NH:6]1

Participants

6

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 687856051-(2-Chloro-1,1-dimethyl-ethyl)-3-(4-methyl-pyridin-3-yl)-urea

Product 1

HCID 596361394,4-Dimethyl-1-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 94.33%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-Chloro-1,1-dimethyl-ethyl)-3-(4-methyl-pyridin-3-yl)-urea (I-200d: 1 g, 4.149 mmol) in dry THF (5 mL) was added dropwise to a stirred mixture of NaH (298 mg, 6.208 mmol) in dry THF (10 mL) under argon atmosphere over a period of 10 minutes at 0° C. The resulting reaction mixture was stirred for 2 hrs. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was partitioned between water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated to afford 800 mg of the product (94.33% yield).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was partitioned between water and ethylacetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7aa77577483943f68191e652e8008da6
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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