(Diethylamino)sulfur trifluoride → HCID 66705592, compound

HRID 425344Notes

Reaction equation

HRID 425344 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([C:20]2[N:21]([S:31]([N:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])[CH:22]=[C:23]([CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])[N:24]=2)O)=[CH:13][CH:12]=1>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([C:20]2[N:21]([S:31]([N:34]([CH3:36])[CH3:35])(=[O:33])=[O:32])[CH:22]=[C:23]([CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])[N:24]=2)[F:7])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 66705597HCID 66705597, compound

Product 1

HCID 66705592HCID 66705592, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride (7.01 mL, 53.5 mmol) was added to an ambient temperature solution of 2-[2-(4-bromophenyl)-1-hydroxyethyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (4.89 g, 10.7 mmol) in methylene chloride (100 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-30% ethyl acetate/hexane afforded 2-[2-(4-bromophenyl)-1-fluoroethyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-755e2a1fd5a644118d8678f5db5ba562
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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