Dimethyl Sulfoxide → HCID 22010728, compound

HRID 323174Notes

Reaction equation

HRID 323174 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]([NH:26][C:27]3[CH:46]=[CH:45][C:30]([C:31]([N:33]([CH3:44])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH2:41][CH2:42][OH:43])=[O:32])=[CH:29][CH:28]=3)=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:19]([C:24]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([C:31]([N:33]([CH3:44])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH2:41][CH:42]=[O:43])=[O:32])=[CH:45][CH:46]=3)=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22010926HCID 22010926, compound

Product 1

HCID 22010728HCID 22010728, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (127 mg) in dichloromethane (20 ml) was added dimethyl sulfoxide (78 mg) at −78° C. and the solution was stirred at the same temperature for 10 minutes. A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(2-hydroxyethoxy)phenyl]benzamide (400 mg) in dichloromethane (5 ml) was added to the mixture at −78° C. After being stirred at −78° C. for 20 minutes, triethylamine (0.50 ml) was added to the mixture at the same temperature and the cooling bath was removed. The mixture was stirred at ambient temperature for 3 hours and the solution was washed successively with 1N hydrochloric acid, water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(formylmethyloxy)phenyl]benzamide (399 mg) as an amorphous. To a mixture of the crude obtained aldehyde (399 mg) and hydroxylamine hydrochloride (174 mg) in ethanol (20 ml) was added potassium carbonate (173 mg) in water (2 ml) and the solution was stirred at ambient temperature for 2 hours. The mixture was diluted with ethyl acetate (30 ml) and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(2-hydroxyiminoethoxy)phenyl]benzamide (288 mg) as an amorphous.

Workup

  1. stirringAfter being stirred at −78° C. for 20 minutes
  2. customthe cooling bath was removed
  3. stirringThe mixture was stirred at ambient temperature for 3 hours
  4. washthe solution was washed successively with 1N hydrochloric acid, water and brine
  5. dry with materialThe organic solution was dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ed73ce7538444f3b85841039722a6f5a
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

Loading…