Iodoethane → HCID 15949655, compound

HRID 646268Notes

Reaction equation

HRID 646268 reaction equation
[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]([C:14]2[CH:15]=[C:16]([CH:19]=[O:20])[NH:17][CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=2)[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:30][CH3:31]>CN(C=O)C.C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]([C:14]2[CH:15]=[C:16]([CH:19]=[O:20])[N:17]([CH2:30][CH3:31])[CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=2)[N:6]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 15949654HCID 15949654, compound

Product 1

HCID 15949655HCID 15949655, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF, (7 mL) is dissolved 4-[2-amino-4-(3-bromophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-1H-pyrrole-2-carbaldehyde (1.50 g; 4.15 mmol). To this solution is added cesium carbonate (1.35 g; 4.15 mmol) and iodoethane (0.43 mL; 5.4 mmol), and the mixture is stirred for 20 hours at room temperature. The mixture is diluted to 50 mL with chloroform, washed twice with water, dried over MgSO4, filtered, and evaporated. The residue was crystallized in ethyl acetate to give the title product as light-brown crystals, 1.18 g (73% yield), mp 194-195° C.; MS (ES) m/z 387.0, [M−H]−.

Workup

  1. washwashed twice with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized in ethyl acetate

Sources & evidence

ORD record
ord-3aa98d7f943e444b8d6eca45dcabac24
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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