3-Bromoaniline → 3-(3-Bromophenylamino)-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione

HRID 2084985Notes

Reaction equation

HRID 2084985 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[C:11](=[O:23])[NH:12][C:13](=[O:22])[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[C:11](=[O:23])[NH:12][C:13](=[O:22])[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 112879523-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione

Product 1

HCID 99516683-(3-Bromophenylamino)-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-bromoaniline (227 mL, 0.020 mol) and 3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione (2.02 g, 0.0083 mol; prepared by analogy with the methods described in WO97/34890 and Wiley, R P H, and Slaymaker, S. C. J. Am. Chem. Soc (80) 1385 (1958)) in methanol (50 mL) was heated at reflux for 40 hours, cooled and concentrated. The residue was acidified with aqueous hydrochloric acid (1M, 200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic solutions were washed with water and brine, dried with magnesium sulphate, evaporated and the residue chromatographed on silica gel using dichloromethane-diethyl ether (gradient from 100:0 to 95:5 v/v) as eluent to afford the title compound as a solid.

Workup

  1. customprepared by analogy with the methods
  2. temperatureat reflux for 40 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. washThe combined organic solutions were washed with water and brine
  7. dry with materialdried with magnesium sulphate
  8. customevaporated
  9. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-b98e98e237b141459aae2a73dbad1912
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

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