Water → HCID 68674456, compound

HRID 1927685Notes

Reaction equation

HRID 1927685 reaction equation
[H-].[Na+].[I:3][C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[NH:7][CH:8]=1.[CH3:23][N:24]([CH3:29])[S:25](Cl)(=[O:27])=[O:26].O>CN(C)C=O.C(Cl)Cl.CC(C)=O>[I:3][C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:15][CH:16]=2)[N:7]([S:25]([N:24]([CH3:29])[CH3:23])(=[O:27])=[O:26])[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 178506558HCID 178506558, compound

Product 1

HCID 68674456HCID 68674456, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (384 mg, 16 mmol) was added to a solution of 2-{4-[2-(4-iodo-1H-imidazol-2-yl)ethyl]phenyl}pyridine (5 g, 13.3 mmol) in dimethylformamide (100 mL) at 0° C. After stirring at 0° C. for 1 hr, dimethylsulfamoyl chloride (2.15 mL, 20 mmol) was added. After stirring at rt overnight, the reaction mixture was poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried (sodium sulfate) and concentrated to give a residue. Chromatography of the residue over silica gel eluting with 0-20% acetone methylene chloride afforded 4-iodo-N,N-dimethyl-2-[2-(4-pyridin-2-ylphenyl)ethyl]-1H-imidazole-1-sulfonamide.

Workup

  1. stirringAfter stirring at rt overnight
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give a residue

Sources & evidence

ORD record
ord-adbb8d9ba11c4b7485a0d4d78bb10712
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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