4-Chloroaniline → HCID 21912462, compound

HRID 1245423Notes

Reaction equation

HRID 1245423 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH2:12][CH3:13])[N:3]=1.[Cl:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C(O)C>[Cl:10][C:6]1[N:5]=[C:4]([S:11][CH2:12][CH3:13])[N:3]=[C:2]([NH:19][C:18]2[CH:20]=[CH:21][C:15]([Cl:14])=[CH:16][CH:17]=2)[C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 21912473HCID 21912473, compound

Product 1

HCID 21912462HCID 21912462, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from step (iii) (4 g) and 4-chloroaniline (5.3 g) in ethanol (40 ml) was heated under reflux for 16 h then the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and 2M hydrochloric acid, the organics washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 10–15% ethyl acetate in isohexane. Yield 4.99 g

Workup

  1. temperatureunder reflux for 16 h
  2. customthe solvent removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and 2M hydrochloric acid
  4. washthe organics washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by chromatography on silica eluting with 10–15% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-e4961e20803d47c6826ddc5125489f60
Source dataset
uspto-grants-2006_10
Patent number
US07125881B2

Reaction notes

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