Hydrochloric Acid → HCID 178501779, compound

HRID 1593229Notes

Reaction equation

HRID 1593229 reaction equation
Cl.Cl[CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([CH3:13])=[CH:6][N:5]=1.[SH:14][C:15]1[NH:16][C:17]2[C:23]([S:24]([C:27]3[C:38]([CH3:39])=[CH:37][C:30]([O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:29][C:28]=3[CH3:40])(=[O:26])=[O:25])=[C:22]([O:41][CH3:42])[CH:21]=[CH:20][C:18]=2[N:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:42][O:41][C:22]1[CH:21]=[CH:20][C:18]2[N:19]=[C:15]([S:14][CH2:3][C:4]3[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([CH3:13])=[CH:6][N:5]=3)[NH:16][C:17]=2[C:23]=1[S:24]([C:27]1[C:28]([CH3:40])=[CH:29][C:30]([O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:37][C:38]=1[CH3:39])(=[O:25])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideHCID 178501780HCID 178501780, compound2×

Product 1

HCID 178501779HCID 178501779, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride (4.4 g, 0.020 mol) was added to a mixture of methyl {4-[(2-mercapto-5-methoxybenzimidazolyl)sulfonyl]-3,5-dimethylphenoxy}acetate (Intermediate A4, 8.2 g, 0.019 mol), potassium carbonate (5.7 g, 0.041 mol), and dimethylformamide (80 mL). The mixture was stirred for 1.5 hr and was then poured in 150 mL of rapidly stirring ice water containing 40 mL of 1.2 M hydrochloric acid. The resulting solid was collected and washed with several portions of water. After partial air-drying, the 10 g of solid was dissolved in 100 mL of dichloromethane. This solution was washed with saturated aqueous sodium bicarbonate, filtered through 1PS paper, and concentrated. The residue was mixed with boiling methanol and collected, yielding 8.9 g (80%) of the title compound.

Workup

  1. customThe resulting solid was collected
  2. washwashed with several portions of water
  3. dissolutionAfter partial air-drying, the 10 g of solid was dissolved in 100 mL of dichloromethane
  4. washThis solution was washed with saturated aqueous sodium bicarbonate
  5. filtrationfiltered through 1PS paper
  6. concentrationconcentrated
  7. additionThe residue was mixed with boiling methanol
  8. customcollected

Sources & evidence

ORD record
ord-70b70875288e438c8d516bcded75fadc
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

Loading…