Dimethyl Sulfoxide → HCID 6484105, compound

HRID 1828194Notes

Reaction equation

HRID 1828194 reaction equation
[C:1](Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]1([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([CH2:24][OH:25])=[CH:23][C:18]=3[N:17]([CH3:26])[C:16]2=[O:27])CC[CH2:12]1.C(N(CC)CC)C>ClCCl>[CH2:11]([N:15]1[C:19]2[CH:20]=[CH:21][C:22]([CH:24]=[O:25])=[CH:23][C:18]=2[N:17]([CH2:26][CH3:1])[C:16]1=[O:27])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 17952496HCID 17952496, compound

Product 1

HCID 6484105HCID 6484105, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a dichloromethane (50 mL) solution of oxalyl chloride (1.47 mL, 16.8 mmol) at −78° C. was added methyl sulfoxide (1.47 mL, 20.5 mmol). After 15 minutes 1-Cyclobutyl-5-hydroxymethyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (2.21 g, 10.0 mmol, in 20 mL dichloromethane) was added. After 20 minutes triethylamine (4.26 mL, 20.6 mmol) was added and the reaction was allowed to warm to 23° C. Upon dilution with saturated sodium bicarbonate and dichloromethane the product was extracted into dichloromethane. The organic layer was dried over sodium sulfate and concentrated to give 1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde (2.17 g).

Workup

  1. extractionUpon dilution with saturated sodium bicarbonate and dichloromethane the product was extracted into dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-75209fc55e4f4d2988fbd5b196ba2001
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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