Hydrochloric Acid → HCID 10787804, compound

HRID 275984Notes

Reaction equation

HRID 275984 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Cl.[I:18]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O.C(O)C>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]([I:18])[CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 18316767HCID 18316767, compound

Product 1

HCID 10787804HCID 10787804, compoundYield 53.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of ethyl N-[4-(2-bromoethyl)-phenyl]aminoacetate (580 mg) in acetonitrile (4.05 ml) were added concentrated hydrochloric acid (169 μl) and N-iodosuccinimide (912 mg) under ice-cooling, and the mixture was stirred for 1 hour. Ethanol (4.0 ml) was added to the reaction mixture, and the mixture was stirred for 45 minutes under ice-cooling. A solution of sodium thiosulfate (640 mg) in water (20 ml) was added to the reaction mixture, and the mixture was stirred for 1 hour under ice-cooling. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=9/1) gave ethyl N-[4-(2-bromoethyl) -2-iodophenyl]aminoacetate (449 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 45 minutes under ice-
  3. temperaturecooling
  4. stirringthe mixture was stirred for 1 hour under ice-
  5. temperaturecooling
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed in vacuo
  10. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-8f7963cdb8c84e28b6b603d8dceb168c
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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