Potassium Carbonate → HCID 53837479, compound

HRID 1904754Notes

Reaction equation

HRID 1904754 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[C:8]([CH2:13]Cl)[N:9]=[CH:10][CH:11]=2)[S:6][CH:5]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[SH:19][C:20]1[NH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.[C:29]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CO.ClCCl>[CH3:29][O:3][C:1]([C:4]1[C:12]2[C:7](=[C:8]([CH2:13][S:19][C:20]3[NH:21][C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)[N:9]=[CH:10][CH:11]=2)[S:6][CH:5]=1)=[O:2]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 54085379HCID 54085379, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 53837479HCID 53837479, compoundYield 81.5%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 110 mg (0.483 mmol) of 3-carboxy-7-chloromethylthieno[2, 3-c]pyridine (i -5), 2 ml of dichloromethane and 2 drops of anhydrous DMF was added 0.1 ml (2.8 equivalents) of thionyl chloride, and the mixture was stirred for 2.5 hr. at room temperature. Then the solution was treated with 3 ml of anhydrous methanol, stirred for 30 min. at room temperature and refluxed for 2 min. After concentration under reduced pressure, 2 ml of anhydrous DMF, 88 mg (1.2 equivalents) of 2-mercaptobenzimidazole and 536 mg (8 quivalents) of anhydrous K2CO3 were added to the solution and the mixture was stirred for 4 hr. at room temperature. After concentration under reduced pressure, the mixture was extracted with ethyl acetate and subjected to silica gel column chromatography, eluting with CH2Cl2 --ethyl acetate. From the eluate, 140 mg (Yield : 81.5%) of 2-[(3-methoxycarbonylthieno[2, 3-c]pyridin-7-yl)methylthio]benzimidazole (Ia-10) was obtained as a foamy product.

Workup

  1. customat room temperature
  2. stirringstirred for 30 min. at room temperature
  3. temperaturerefluxed for 2 min
  4. additionwere added to the solution
  5. stirringthe mixture was stirred for 4 hr
  6. customat room temperature
  7. concentrationAfter concentration under reduced pressure
  8. extractionthe mixture was extracted with ethyl acetate
  9. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-cfc2f236d028416683c8e8c32387db17
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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