Sodium Bicarbonate → HCID 45279096, compound

HRID 238959Notes

Reaction equation

HRID 238959 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]([CH2:26][CH2:27]O)=[CH:24][C:23]([C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=3)=[O:30])=[C:22]2[CH3:42])=[C:17]([CH3:43])[CH:16]=1.C(=O)([O-])O.[Na+]>ClCCl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]([CH2:26][CH2:27][F:11])=[CH:24][C:23]([C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=3)=[O:30])=[C:22]2[CH3:42])=[C:17]([CH3:43])[CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 67377695HCID 67377695, compound

Product 1

HCID 45279096HCID 45279096, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of bis(2-methoxyethyl)aminosulfur trifluoride (11 ml, 61 mmol) in dichloromethane (200 ml), a solution of the above 1-(4-chloro-2-methylphenyl)-5-(2-hydroxyethyl)-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide (6.8 g, 15 mmol) in dichloromethane (200 ml) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured to a saturated aqueous sodium hydrogencarbonate solution cooled to 0° C., and the mixture was stirred at room temperature for 15 minutes. The organic layer was washed with saturated brine, and after it was dried with magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=4:1) to give the title compound (3.8 g, 56%) as a solid.

Workup

  1. temperaturecooled to 0° C.
  2. stirringthe mixture was stirred at room temperature for 15 minutes
  3. washThe organic layer was washed with saturated brine
  4. dry with materialafter it was dried with magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b16c2028c5bc46a985f14efe6254b34d
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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