Dimethyl Sulfoxide → HCID 22010728, compound

HRID 323171Notes

Reaction equation

HRID 323171 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 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (174 mg) in dichloromethane (15 ml) was added dimethyl sulfoxide (107 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 (440 mg) in dichloromethane (5 ml) was added to the mixture at −78° C. After being stirred at −78° C. for 20 minutes, triethylamine (0.51 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-(formylmethoxy)phenyl]benzamide (420 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-7cb03f9bc33443c4b7389ba782a11752
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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