Sodium Bicarbonate → HCID 178498675, compound

HRID 723148Notes

Reaction equation

HRID 723148 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:22][CH3:23])=[C:8]([S:10]([C:13]2[CH:18]=[C:17]([Cl:19])[C:16]([NH2:20])=[C:15]([NH2:21])[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[C:24]([O-])(O)=O.[Na+]>C(O)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:22][CH3:23])=[C:8]([S:10]([C:13]2[CH:18]=[C:17]([Cl:19])[C:16]3[NH:20][CH:24]=[N:21][C:15]=3[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69586305HCID 69586305, compound

Product 1

HCID 178498675HCID 178498675, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The refrigerated solution of 4-(3,4-diamino-5-chloro-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((from above step b) 0.224 g, 0.570 mmol) in formic acid (4.5 mL) from above was allowed to slowly warm to room temperature and then heated to reflux (110° C.) 3 h. The mixture was cooled to room temperature and poured over ice. The pH was adjusted to pH 8 by carefully adding solid NaHCO3 portionwise with stirring. The aqueous solution was extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed in vacuo to afford the product 4-(7-chloro-1H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (0.201 g, 87%) as a brown foamy solid. The crude material was used directly in the next reaction.

Workup

  1. temperatureheated
  2. temperatureto reflux (110° C.) 3 h
  3. temperatureThe mixture was cooled to room temperature
  4. additionpoured over ice
  5. extractionThe aqueous solution was extracted with EtOAc (2×150 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-04112377ca1649d6987f5cb111624516
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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