2-Amino-5-chlorobenzonitrile → HCID 24762633, compound

HRID 2356988Notes

Reaction equation

HRID 2356988 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>CN1C(=O)CCC1>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=2[C:4]#[N:5])(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 800192-Amino-5-chlorobenzonitrileHCID 1398824-t-Butylbenzenesulfonyl chloride

Product 1

HCID 24762633HCID 24762633, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 0.15 g of 2-amino-5-chloro-benzonitrile and 0.23 g of 4-tert.butyl-benzenesulfonyl chloride is dissolved in 2 ml of NMP (N-methyl 2-pyyrolidone) and cooled in an ice bath to 5°. 2.5 ml of a solution of potassium-tert.butylat (1 N in THF) is added, the mixture obtained is stirred for 30 min, quenched with water and from the mixture obtained solvent is evaporated. The evaporation residue is dissolved in EtAc, washed with saturated NaHCO3 solution and dried. Solvent is evaporated and the evaporation residue is subjected to chromatography on a reversed phase column. 4-tert.Butyl-N-(4-chloro-2-cyano-phenyl)-benzenesulfonamide is obtained.

Workup

  1. temperaturecooled in an ice bath to 5°
  2. customthe mixture obtained
  3. customquenched with water and from the mixture
  4. customobtained solvent
  5. customis evaporated
  6. dissolutionThe evaporation residue is dissolved in EtAc
  7. washwashed with saturated NaHCO3 solution
  8. customdried
  9. customSolvent is evaporated

Sources & evidence

ORD record
ord-65de80ac7f0d45308d49e407a746c788
Source dataset
uspto-grants-2010_07
Patent number
US07759390B2

Reaction notes

Loading…