4-Bromoaniline → (4-Bromo-phenyl)-[4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-YL]-amine

HRID 1591604

Reaction equation

HRID 1591604 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[CH3:16])[N:3]=1.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.O1CCCC1.C(N(C(C)C)CC)(C)C>ClCCl>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]3[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=3[CH3:16])[N:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 78074-BromoanilineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 858270322,4-Dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine

Product 1

HCID 10179730(4-Bromo-phenyl)-[4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-YL]-amineYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,4-dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine (2.5 g, 9.1 mmol), 4-bromoaniline (1.6 g, 9.3 mmol), tetrahydrofuran (60 ml), and diisopropylethylamine (1.6 ml, 9.2 mmol) was stirred for 1 hour. The solution was treated with dichloromethane (200 ml), washed with saturated aqueous sodium chloride solution (50 ml), and concentrated under reduced pressure. The residual solid was treated with hydrochloric acid (1 M, 25 ml) and stirred vigorously for 30 minutes. Filtration and drying under reduced pressure provided the title compound (3.2 g, 86% yield). 1H NMR (DMSO-d6) 10.75-10.80 (m, 1H), 7.85-7.92 (m, 1H), 7.50-7.65 (m, 4H), 7.40 (m, 1H), 2.58 (s, 3H).

Workup

  1. washwashed with saturated aqueous sodium chloride solution (50 ml)
  2. concentrationconcentrated under reduced pressure
  3. additionThe residual solid was treated with hydrochloric acid (1 M, 25 ml)
  4. stirringstirred vigorously for 30 minutes
  5. filtrationFiltration
  6. customdrying under reduced pressure

Sources & evidence

ORD record
ord-ec9c63b4008d4545afc3b75be5eac89b
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Linked notes

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