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

HRID 1815901Notes

Reaction equation

HRID 1815901 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 eluted through a 17×2.5 cm column of silica gel (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. washThe crude was eluted through a 17×2.5 cm column of silica gel (25%, 40%, 60% EtOAc/Hexane step gradient)

Sources & evidence

ORD record
ord-e5548e650bd94c75ad43ba71e80b2029
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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