Dichloromethane → N-isopropyl-N-methyl-1H-imidazole-1-carboxamide

HRID 1812402Notes

Reaction equation

HRID 1812402 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[CH2:13](Cl)Cl>>[CH:12]([N:8]([CH3:9])[C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2])([CH3:11])[CH3:13]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 66611115N-isopropyl-N-methyl-1H-imidazole-1-carboxamideYield 80%

Conditions

Temperature
0 °C

Procedure

To a 50 mL round-bottomed flask was added 1,1′-carbonyldiimidazole (1.663 g, 10.25 mmol), (Fluka Chemie) DCM (25 mL). The solution was stirred at 0° C. using a water bath and treated in one portion with n-isopropylmethylamine (0.5 mL, 6.84 mmol) (Aldrich). The water bath was removed, and the solution was stirred at room temperature. After 2 hours all starting material was consumed. The reaction mixture was diluted with DCM (10 mL) and quenched with water. The organic layer was separated, dried over sodium sulfate and concentrated to afford N-isopropyl-N-methyl-1H-imidazole-1-carboxamide (0.920 g, 5.50 mmol, 80% yield).

Workup

  1. customThe water bath was removed
  2. stirringthe solution was stirred at room temperature
  3. customAfter 2 hours all starting material was consumed
  4. additionThe reaction mixture was diluted with DCM (10 mL)
  5. customquenched with water
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-efc067954ef04f51b203211d9125d83d
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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