3,4,5-Trimethoxyaniline → HCID 22329688, compound

HRID 586155Notes

Reaction equation

HRID 586155 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:15][C:14](=O)[C:13]3=[C:17]([CH3:21])[N:18]=[C:19]([CH3:20])[N:12]3[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[NH2:27]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[C:14]([NH:27][C:26]3[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:24]([O:23][CH3:22])[CH:25]=3)[C:13]3=[C:17]([CH3:21])[N:18]=[C:19]([CH3:20])[N:12]3[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 135553064HCID 135553064, compound

Product 1

HCID 22329688HCID 22329688, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 30 mg (0.08 mmol) of the compound of Example 33A with 100 mg (0.55 mmol) of 3,4,5-trimethoxyaniline is stirred in the form of a melt for 16 hours at a bath temperature of 120° C. It is taken up in ethyl acetate, washed with water, dried and concentrated. After purification on a silica gel column using dichloromethane/ethyl acetate [lacuna] to 2:1 and filtering off with suction using ether/heptane, 28.6 mg (43.31% of theory) of almost colourless crystals are obtained.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customAfter purification on a silica gel column
  5. filtrationfiltering off with suction
  6. customare obtained

Sources & evidence

ORD record
ord-ebf556c997274ebe8820a88e44b082e5
Source dataset
uspto-grants-2005_08
Patent number
US06936609B2

Reaction notes

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