Cesium carbonate → Ethyl 1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole-2-carboxylate

HRID 714625Notes

Reaction equation

HRID 714625 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=1[CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=1[CH2:17][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[C:6]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 178470305HCID 178470305, compound

Product 1

HCID 67409298Ethyl 1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

1000 mg (5.4 mmol) of ethyl 4-nitro-1H-imidazole-2-carboxylate together with 1426 mg (5.94 mmol) of 2,6-dichlorobenzyl bromide were dissolved in 37 ml of DMF, and 2112 mg (6.48 mmol) of cesium carbonate were added. The mixture was stirred at 75° C. for 4 h. After cooling to RT, the mixture was added to 100 ml of ice-water. The precipitated product was filtered off and washed with water. The beige solid was dried under high vacuum. This gave 1500 mg (81% of theory) of the target compound.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water
  4. customThe beige solid was dried under high vacuum

Sources & evidence

ORD record
ord-f8359717da2d43debd6cb421c50285b0
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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