Chlorosuccinimide → HCID 10062233, compound

HRID 486669

Reaction equation

HRID 486669 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17])[NH:10][CH3:11].[Cl:18]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:18])=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17])[NH:10][CH3:11]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 130176Compound 7189

Product 1

HCID 10062233HCID 10062233, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 8 g of 2-amino-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine in 40 ml of N,N-dimethylformamide was treated with a solution of 6.41 g of N-chlorosuccinimide in 40 ml of N,N-dimethylformamide and then stirred at room temperature for 8 hours. Evaporation of the volatiles afforded an oil which was decanted into 100 ml of water, basified with 30 ml of 10% aqueous sodium hydroxide and extracted with dichloromethane (2×100 ml). The extract was washed with water (2×100 ml), dried over anhydrous sodium sulfate and concentrated. Thin layer chromatography of the resultant oil indicated a multicomponent mixture. Purification of the mixture was accomplished by successive HPLC separations (Water's Associates Prep LC/System 500, silica gel, elution with methanol). Concentration of the appropriate fractions afforded a residue which was dissolved in diethyl ether, filtered free of insolubles and concentrated. The resultant oil crystallized upon standing to yield 1.05 g of 2-amino-5-chloro-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, mp 59°-61° C.

Workup

  1. customEvaporation of the volatiles
  2. customafforded an oil which
  3. customwas decanted into 100 ml of water
  4. extractionextracted with dichloromethane (2×100 ml)
  5. washThe extract was washed with water (2×100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customPurification of the mixture
  9. washwas accomplished by successive HPLC separations (Water's Associates Prep LC/System 500, silica gel, elution with methanol)
  10. customConcentration of the appropriate fractions afforded a residue which
  11. filtrationfiltered free of insolubles
  12. concentrationconcentrated
  13. customThe resultant oil crystallized

Sources & evidence

ORD record
ord-dff2f7e39068414cb4ed04eb86478962
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Linked notes

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