Cerium(III) chloride → HCID 59140412, compound

HRID 425353Notes

Reaction equation

HRID 425353 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([C:15]2[N:16]([S:26]([N:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])[CH:17]=[C:18]([CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH3:23])[N:19]=2)=[O:14])=[CH:8][CH:7]=1.[CH3:32][Mg]Br>O1CCCC1>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([C:15]2[N:16]([S:26]([N:29]([CH3:31])[CH3:30])(=[O:27])=[O:28])[CH:17]=[C:18]([CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH3:23])[N:19]=2)([OH:14])[CH3:32])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 59140370HCID 59140370, compound2×HCID 178418573HCID 178418573, compound

Product 1

HCID 59140412HCID 59140412, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cerium Chloride (1.625 g, 6.59 mmol) was added to an ambient temperature solution of 2-[(4-bromophenyl)acetyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (Intermediate 8) (1 g, 2.2 mmol) in tetrahydrofuran (22 mL). After stirring at ambient temperature for 1 h, the reaction mixture was cooled to 0° C. and methylmagnesium bromide (3 M in diethyl ether) (2.2 mL, 6.59 mmol) was added. After stirring at 0° C. for a further 30 min, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 2-[2-(4-bromophenyl)-1-hydroxy-1-methylethyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. stirringAfter stirring at 0° C. for a further 30 min
  3. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef41b510d3544424a6ef02f83ae43637
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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