5-Chloro-2-methylaniline → HCID 22496103, compound

HRID 983443Notes

Reaction equation

HRID 983443 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[Cl:18][C:19]1[CH:20]=[C:21]([C:23]([CH3:26])=[CH:24][CH:25]=1)[NH2:22]>CN(C=O)C>[Cl:18][C:19]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:21]([NH:22][C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 72605-Chloro-2-methylanilineHCID 178102,4-Dichloro-1,3,5-triazineHCID 81531Diisopropylethylamine

Product 1

HCID 22496103HCID 22496103, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Dichloro-1,3,5-triazine (3 g, 20 mmol) was dissolved in DMF (20 mL) under N2 and cooled to 0° C. DIEA (2.58 g, 20 mmol) was added, followed by 3-chloro-6-methylaniline (2.83 g, 20 mmol). The reaction solution was stirred with gradual warming to RT. The reaction was quenched after 3 h with water, then extracted 3 times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered, and concentrated. The crude was purified by silica gel chromatography (25%, 40%, 60% EtOAc/Hexane step gradient) giving (5-chloro-2-methyl-phenyl)-(4-chloro-[1,3,5]triazin-2-yl)-amine as a white solid.

Workup

  1. temperaturewith gradual warming to RT
  2. customThe reaction was quenched after 3 h with water
  3. extractionextracted 3 times with EtOAc
  4. washThe EtOAc extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by silica gel chromatography (25%, 40%, 60% EtOAc/Hexane step gradient)

Sources & evidence

ORD record
ord-e462f1c59d3d47a49953cbdd6f9c0577
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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