Sulfuryl chloride → HCID 57800294, compound

HRID 913584Notes

Reaction equation

HRID 913584 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]1[CH:20]=[CH:19][C:11]2[NH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[N:14][C:10]=2[CH:9]=1.C([O-])(O)=O.[Na+]>CC(O)=O.CCOC(C)=O.O>[Cl:4][C:9]1[C:10]2[N:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[NH:12][C:11]=2[CH:19]=[CH:20][C:8]=1[O:7][CH3:6]

Participants

7

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 178488085HCID 178488085, compound

Product 1

HCID 57800294HCID 57800294, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sulfuryl chloride (0.39 mL, 4.86 mmol) was added dropwise to a 0° C. solution of 5-(methyloxy)-2-(trifluoromethyl)-1H-benzimidazole (1.0 g, 4.63 mmol) in HOAc (10 mL). The ice bath was removed and the mixture was allowed to stir at rt for 2 h. The concentrated reaction mixture was suspended in a mixture of EtOAc and H2O and the pH was adjusted to 7 with saturated aqueous NaHCO3. The reaction was partitioned and the aqueous portion was extracted with EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound (0.93 g): MS (ESI) m/z 251 (M+1).

Workup

  1. customThe ice bath was removed
  2. customThe concentrated reaction mixture
  3. customThe reaction was partitioned
  4. extractionthe aqueous portion was extracted with EtOAc
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e89ff9bd5b1945dd89255e2146f0ff7e
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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