Imidazole → HCID 58941238, compound

HRID 747631Notes

Reaction equation

HRID 747631 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.C([C:10]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:11]=1[S:20]([N:23]([CH2:40][CH2:41]Br)[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[CH2:31][C:32]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=1[F:39])(=[O:22])=[O:21])C>CN(C)C=O.C(OCC)(=O)C>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:23]([CH2:40][CH2:41][N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)[S:20]([C:11]2[CH:12]=[CH:13][C:14]([O:18][CH3:19])=[C:15]([O:16][CH3:17])[CH:10]=2)(=[O:22])=[O:21])=[C:25]([CH2:31][C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2[F:39])[CH:26]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 69223225HCID 69223225, compound

Product 1

HCID 58941238HCID 58941238, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 2 ml of dimethylformamide are added, at room temperature, 51 mg of sodium hydride at 50% in oil, followed by 72 mg of imidazole. After 30 minutes at this temperature, 0.4 g of ethyl N-(2-bromoethyl)-N-[2-(2,6-difluorobenzyl)-4-chlorophenyl]-3,4-dimethoxybenzenesulfonamide dissolved in 5 ml of dimethylformamide is introduced. The reaction medium is left for 18 hours at room temperature and then taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 97/3 (v/v) toluene/ethyl acetate mixture to give 0.082 g of the expected product.

Workup

  1. additionis introduced
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a 97/3 (v/v) toluene/ethyl acetate mixture

Sources & evidence

ORD record
ord-0c7f4fe333b34acc803a90e1aa4666c5
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

Loading…