Diethylamine → HCID 178464205, compound

HRID 1591103Notes

Reaction equation

HRID 1591103 reaction equation
[CH2:1]([N:3](S(F)(F)F)[CH2:4][CH3:5])[CH3:2].[C:10]([C:12]1[NH:16][C:15]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[Cl:28])=[N:14][C:13]=1[C:29]([OH:31])=O)#[N:11].[F-].[K+].C(NCC)C>COCCOCCOC.ClCCl>[CH2:1]([N:3]([CH2:4][CH3:5])[C:29]([C:13]1[N:14]=[C:15]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:25])([F:27])[F:26])=[CH:19][C:18]=2[Cl:28])[NH:16][C:12]=1[C:10]#[N:11])=[O:31])[CH3:2]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 123472(Diethylamino)sulfur trifluorideHCID 522689Potassium FluorideHCID 178510663HCID 178510663, compound

Product 1

HCID 178464205HCID 178464205, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8150DiglymeSolvent

Conditions

Temperature
0 °C

Procedure

Diethylaminosulphur trifluoride (1.5 ml) was added dropwise to a stirred suspension of 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole-4-carboxylic acid (1.4 g, 0.004 mol) in 2-methoxyethyl ether (11 ml) whilst maintaining the temperature at about 0° C. Potassium fluoride (0.67 g, 0.0115 mol) was added and the mixture was stirred at 0° C. for 0.5 hours, and added slowly to a solution of diethylamine (8.8 g, 12.5 ml, 0.12 mol) in dichloromethane (75 ml) whilst maintaining the temperature in the range 0°-5° C. The mixture was stirred at 0°-5° C. for 1 hour and at room temperature for 0.5 hours. The mixture was washed with saturated aqueous sodium bicarbonate solution (50 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The residue was purified by mplc on silica eluting with a mixture of ethyl acetate and dichloromethane (1:2) to give N,N-diethyl 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole-4-carboxamide (0.26 g) m.p. 195°-197° C. as an off-white solid.

Workup

  1. temperaturewhilst maintaining the temperature in the range 0°-5° C
  2. stirringThe mixture was stirred at 0°-5° C. for 1 hour and at room temperature for 0.5 hours
  3. washThe mixture was washed with saturated aqueous sodium bicarbonate solution (50 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. customThe residue was purified by mplc on silica eluting with a mixture of ethyl acetate and dichloromethane (1:2)

Sources & evidence

ORD record
ord-0d357d1937af493d91cc192f25402096
Source dataset
uspto-grants-1993_04
Patent number
US05206257

Reaction notes

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