Sodium Bicarbonate → HCID 58700468, compound

HRID 723070Notes

Reaction equation

HRID 723070 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]([Br: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]([Br:19])[C:16]3[N:20]=[CH:24][NH:21][C:15]=3[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69586669HCID 69586669, compound

Product 1

HCID 58700468HCID 58700468, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-(3,4-Diamino-5-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((Example 38, step d) 170 mg, 0.39 mmol) was dissolved in formic acid (2.5 mL) and heated to 100° C. for 2 hours. The resulting solution was cooled to room temperature, poured over ice-water slurry, and basified to pH 8 with NaHCO3. This aqueous solution was extracted with ethyl acetate (75 mL, 3×). The organic layer was separated and washed with water, brine, and dried over MgSO4. Solvents were removed in vacuo to afford 100 mg (57%) of 4-(7-bromo-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester as a brown oil. ESI-MS (m/z): Calcd. for C14H11BrN2O4S3: 447 (M+H); found: 447.1 and 449.1.

Workup

  1. temperatureThe resulting solution was cooled to room temperature
  2. extractionThis aqueous solution was extracted with ethyl acetate (75 mL, 3×)
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-f84aa1df1bc943aea135876491849a3c
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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