Lithium Hydroxide → HCID 86677477, compound

HRID 1621089Notes

Reaction equation

HRID 1621089 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9]C)=[O:8])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:4]=[C:3]1[CH3:15].[Li+].[OH-]>C1COCC1.CO>[CH3:14][O:13][C:11]([C:5]1[N:4]=[C:3]([CH3:15])[N:2]([CH3:1])[C:6]=1[C:7]([OH:9])=[O:8])=[O:12]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 14416594HCID 14416594, compound

Product 1

HCID 86677477HCID 86677477, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 1,2-dimethyl-1H-imidazole-4,5-dicarboxylate (1.89 g, 8.91 mmol) in THF (35 mL) and MeOH (15 mL) was added at 0-5° C. LiOH (1M; 9.35 mL, 9.35 mmol). The reaction mixture was stirred at RT for 7 h and the solvents were evaporated in vacuo. The residue was poured into water (20 mL) and ethyl acetate (30 mL). The ethyl acetate phase was washed with water (10 mL). The combined aqueous phases were acidified with hydrochloric acid (1M, 10 mL) and extracted with dichloromethane/MeOH (95:5, 8×60 mL). The dichloromethane/MeOH phases were dried over MgSO4, filtered and evaporated to give the product as colorless solid (1.29 g, 6.51 mmol, 73.1%). MS: M=199.1 (M+H)+

Workup

  1. customthe solvents were evaporated in vacuo
  2. additionThe residue was poured into water (20 mL) and ethyl acetate (30 mL)
  3. washThe ethyl acetate phase was washed with water (10 mL)
  4. extractionextracted with dichloromethane/MeOH (95:5, 8×60 mL)
  5. dry with materialThe dichloromethane/MeOH phases were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1fd860e1dafb4e58874901117b4bc3b5
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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