Triethylamine → HCID 21273214, compound

HRID 1382780Notes

Reaction equation

HRID 1382780 reaction equation
I[C:2]1[N:3]=[C:4]([CH3:17])[N:5]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=1.[CH3:18][N:19]([CH3:24])[C:20](=[O:23])[CH:21]=[CH2:22].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)(Cl)Cl>[CH3:18][N:19]([CH3:24])[C:20](=[O:23])/[CH:21]=[CH:22]/[C:2]1[N:3]=[C:4]([CH3:17])[N:5]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 17587N,N-DimethylacrylamideHCID 21273227HCID 21273227, compound

Product 1

HCID 21273214HCID 21273214, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-iodo-2-methyl-1-(4-methylbenzenesulphonyl)-1H-imidazole (3.62 g), N,N-dimethylacrylamide (1.05 g), palladium (II) acetate (125 mg) and triethylamine (2 ml) in acetonitrile (3 ml) was heated at 120° under nitrogen for 2.5 h. The cooled mixture waspartitioned between chloroform (3×50 ml) and 2N sodium carbonate (75 ml), and the combined organic layers were dried and evaporated in vacuo to leave a solid (ca. 3.0 g). This solid was purified by FCC eluting with chloroform to give the crystalline title compound (1.55 g), m.p. 162°-163°.

Workup

  1. temperaturewas heated at 120° under nitrogen for 2.5 h
  2. customthe combined organic layers were dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-b6d7b17606094541a79e7b5ae969ca95
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

Loading…