Dimethylformamide → HCID 67175048, compound

HRID 2233539Notes

Reaction equation

HRID 2233539 reaction equation
[Na].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:10][C:9](=[O:11])[NH:8][C:7]=2[CH:12]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]C.CN(C)C=O>C(O)C.CS(C)=O>[CH2:2]([C:3]1[CH:4]=[CH:5][C:6]2=[N:10][C:9](=[O:11])[N:8]=[C:7]2[CH:12]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 89191-BromododecaneHCID 2231345-MethylbenzimidazoloneHCID 5360545Sodium

Product 1

HCID 67175048HCID 67175048, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

Sodium (0.05 g, 2.17 mg atom) was dissolved in ethanol (5 ml) and to this was added 6-methyl-1,3-dihydro-benzoimidazol-2-one (0.20 g, 1.35 mmol) and the solution was stirred at room temperature for 1 h. The solvent was removed in vacuo and the white solid was taken up in tetrahydrofuran (5 ml) and dimethyl sulfoxide (5 ml), and to this was added 1-bromododecane (0.34 g, 1.36 mmol) and the whole was stirred at room temperature for 2 h. N,N-Dimethylformamide (5 ml) was added to the mixture and the whole was stirred for a further 2 h. The mixture was filtered and the filtrate was evaporated in vacuo to give a yellow residue. The residue was placed on a silica column and chromatographed with 12.5% hexane-ethyl acetate to give (19) as a yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. stirringthe whole was stirred at room temperature for 2 h
  3. stirringthe whole was stirred for a further 2 h
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated in vacuo
  6. customto give a yellow residue
  7. customchromatographed with 12.5% hexane-ethyl acetate

Sources & evidence

ORD record
ord-b94912cdd3bf48d0a72848e5239570fd
Source dataset
uspto-grants-2010_05
Patent number
US07709514B2

Reaction notes

Loading…