Hydrochloric Acid → HCID 18316763, compound

HRID 275985Notes

Reaction equation

HRID 275985 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:6][CH:5]=1.[ClH:17].[Cl:18]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[C:8]([Cl:17])[C:7]([NH:10][CH2:11][C:12]([N:14]([CH3:15])[CH3:16])=[O:13])=[C:6]([Cl:18])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 18316760HCID 18316760, compound

Product 1

HCID 18316763HCID 18316763, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-[[4-(2-bromoethyl)phenyl]-amino]-N,N-dimethylacetamide (1.13 g) in acetonitrile (11.3 ml) were added concentrated hydrochloric acid (331 μl) and N-chloro-succinimide (1.06 g) under ice-cooling, and the mixture was stirred for 1 hour. A solution of sodium thiosulfate (1.26 g) in water (20 ml) was added to the reaction mixture, and the resulting mixture was stirred for 30 minutes 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=2/1) gave 2-[[4-(2-bromoethyl)-2,6-dichlorophenyl]amino]-N,N-dimethylacetamide (795 mg).

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred for 30 minutes under ice-
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-8f358bcddb4b4e539cc0f9b5a2958615
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

Loading…