1,1-Dichloroethane → HCID 178526356, compound

HRID 858316Notes

Reaction equation

HRID 858316 reaction equation
ClC(Cl)C.[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[O:16][C:17]3[C:23]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:22][CH:21]=[CH:20][C:18]=3[CH:19]=2)=O)[CH:9]=[CH:10][CH:11]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[ClH:35].[NH2:36][OH:37].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[Cl:35][C:19]1[C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:17]=2[O:16][C:15]=1[C:13]([NH:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[CH:7]=1)=[N:36][OH:37]

Participants

8

Reactant 5

HCID 63651,1-DichloroethaneHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 443297Hydroxyamine hydrochlorideHCID 12150613HCID 12150613, compound

Product 1

HCID 178526356HCID 178526356, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a dichloroethane solution of 7-pyrrolidin-1-yl-benzofuran-2-carboxylic acid (3-chloro-phenyl)-amide (343 mg, 1 μM) was added phosphorous pentachloride (210 mg, 1.2 mmol), and the mixture was stirred at 75° C. for 2 hours. The solvent was removed under vacuum, the mixture was treated with 5 ml of toluene and then was evaporated to dryness under vacuum. The residue was dissolved in acetonitrile and was added to another flask containing 210 mg (3 mmol) hydroxylamine hydrochloride and triethyl amine 701 μL (5 mmol) in acetonitrile at 0° C. The mixture was allowed to stir overnight. The reaction mixture was diluted with ethyl acetate, washed with 1 N HCl (2×) and brine. The organic layer was dried over MgSO4, filtered and stripped. The crude product was purified by flash chromatography on silica gel eluted with hexane/ethyl acetate (20:1) to give 43 mg of 3-chloro-N-(3-chloro-phenyl)-N′-hydroxy-7-pyrrolidin-1-yl-benzofuran-2-carboxamidine in 13% yield.

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe mixture was treated with 5 ml of toluene
  3. customwas evaporated to dryness under vacuum
  4. dissolutionThe residue was dissolved in acetonitrile
  5. additionwas added to another flask
  6. stirringto stir overnight
  7. washwashed with 1 N HCl (2×) and brine
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. customThe crude product was purified by flash chromatography on silica gel
  11. washeluted with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-65d21575689442548ff655c65d1ba653
Source dataset
uspto-grants-2006_12
Patent number
US07148259B1

Reaction notes

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