N-Methylethylamine → HCID 25125284, compound

HRID 1363035Notes

Reaction equation

HRID 1363035 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].C(NC)C>ClCCl>[CH2:12]([N:8]([CH3:9])[C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2])[CH3:11]

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 25125284HCID 25125284, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

To the cooled (ice-water bath) suspension of 1,1′-carbonyldiimidazole (178.4 g, 1.10 moles) in dichloromethane (720 mL) was added N-ethylmethylamine (59.1 g, 1 mole) keeping the internal temperature below 10° C. during addition. The reaction mixture was stirred at 20-25° C. for 2-3 hours and then cooled to 0-5° C. The reaction mixture was quenched by slow addition of water (720 mL) keeping the IT<10° C. The aqueous and organic phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were washed with water. The organic phase was concentrated to give N-ethyl-N-methyl-1H-imidazole-1-carboxamide (138 g). 1H NMR (CDCl3) δ7.90 (s, 1H); 7.24 (s, 1H); 7.08 (s, 1H); 3.47 (q, J=7.2 Hz, 2H); 3.07 (s, 3H); 1.27 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureTo the cooled
  2. customthe internal temperature below 10° C.
  3. additionduring addition
  4. temperaturecooled to 0-5° C
  5. customThe reaction mixture was quenched by slow addition of water (720 mL)
  6. customthe IT<10° C
  7. customThe aqueous and organic phases were separated
  8. extractionthe aqueous phase was extracted with dichloromethane
  9. washThe combined organic extracts were washed with water
  10. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-aa77ae3f69574539a8662236b5553be2
Source dataset
uspto-grants-2011_02
Patent number
US07884121B2

Reaction notes

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