Ammonium Hydroxide → HCID 178527552, compound

HRID 1434671Notes

Reaction equation

HRID 1434671 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.C([O-])(=O)C.[Na+].[OH-].[NH4+].[Cl-].[NH4+].[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH:28][S:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH2:38])=[NH:37])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>CN(C=O)C.CCOC(C)=O>[Cl:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[Cl:11])[CH2:4][C:3]1[N:37]=[C:36]([C:35]2[CH:34]=[CH:33][C:32]([S:29]([NH:28][C:24]3[S:23][CH:27]=[CH:26][N:25]=3)(=[O:31])=[O:30])=[CH:40][CH:39]=2)[NH:38][CH:2]=1

Participants

8

Reactant 5

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 517045Sodium AcetateHCID 534032741-Bromo-3-(3,4-dichlorophenyl)propan-2-oneHCID 85978227HCID 85978227, compound

Product 1

HCID 178527552HCID 178527552, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-bromo-3-(3,4-dichloro-phenyl)-propan-2-one (4.1 mmol) in DMF (20 mL) was added sodium acetate (21 mmol) and the mixture was stirred for 2 hr at room temperature before concentrated ammonium hydroxide (5 mL) and ammonium chloride (1 g) were added. After the reaction mixture was stirred for 10 min, 4-(thiazol-2-ylsulfamoyl)-benzamidine (4.1 mmol) was added and the mixture was stirred at 60° C. overnight. After cooled to room temperature, the mixture was diluted with AcOEt (200 mL) and the resulting organic solution was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 4-[4-(3,4-dichloro-benzyl)-1H-imidazol-2-yl]-N-thiazol-2-yl-benzenesulfonamide (3.1 mmol), which was converted to its sodium salt by reacting with NaOH solution (0.999 N).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at 60° C. overnight
  3. washthe resulting organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-7eea7505c2d9496ca2a7543eb4adec1d
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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