Dimethyl Sulfoxide → HCID 22349276, compound

HRID 896389Notes

Reaction equation

HRID 896389 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[C:21]2[N:20]=[C:19]([CH2:22][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]([CH:32]([CH3:34])[CH3:33])[C:24]3=[O:35])[N:18]([CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:17]=2[CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH:32]([N:25]1[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:23]([CH2:22][C:19]2[N:18]([CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([CH:12]=[O:11])[C:21]=3[N:20]=2)[C:24]1=[O:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 20813981HCID 20813981, compound

Product 1

HCID 22349276HCID 22349276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (−45° C.) solution of oxalyl chloride (0.4 mL 2M in dichloromethane, 0.8 mmol) in DCM (5 mL) was added DMSO (115 μL, 1.62 mmol) under a nitrogen atmosphere. After stirring for 3 min. a solution of 1-[4-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (300 mg, 0.738 mmol) in DCM (4 mL) was cannulated and stirring was continued for 15 min. at the same temperature. Then diisopropylethyl amine (643 μL, 3.69 mmol) was added, and the mixture was allowed to warm to room temperature after 5 min. Stirring was continued for 4 hrs, the mixture was quenched with satd. ammonium chloride and the layers separated. The aqueous phase was extracted with DCM, and the combined organic phases washed with water, brine and dried (MgSO4) to afford 2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-4-carbaldehyde as a pale yellow solid (quantitative recovery), that was sufficiently pure for the next steps:

Workup

  1. stirringStirring
  2. waitwas continued for 4 hrs
  3. customthe mixture was quenched with satd
  4. customammonium chloride and the layers separated
  5. extractionThe aqueous phase was extracted with DCM
  6. washthe combined organic phases washed with water, brine
  7. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-4b25acd2bc854a008ed72a3468de2fda
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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