Imidazole → HCID 22228535, compound

HRID 1173109Notes

Reaction equation

HRID 1173109 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:23]=2[NH:22][CH:21]=[C:20]3[Cl:24])(=[O:13])=[O:12])=[CH:7][CH:6]=1.[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.CN(C)C=O>O>[Cl:24][C:20]1[C:19]2[C:23](=[C:15]([NH:14][S:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)=[CH:6][CH:7]=3)(=[O:13])=[O:12])[CH:16]=[CH:17][CH:18]=2)[NH:22][CH:21]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228DimethylformamideHCID 22228591HCID 22228591, compound

Product 1

HCID 22228535HCID 22228535, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 4-(3-bromopropyl)-N-(3-chloro-1H-indole-7-yl)benzenesulfonamide (213 mg, 0.5 mmol) were added 170 mg (2.5 mmol) of imidazole and 6 ml of dimethylformamide, followed by heating at 80° C. for 3 hours in a nitrogen atmosphere. Then, the reaction mixture was poured into water and extracted with chloroform. The extract was dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 160 mg of the title compound.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a70db7919b8748189304bcaec9f77672
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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