3,4,5-Trimethoxyaniline → HCID 22252397, compound

HRID 1611976Notes

Reaction equation

HRID 1611976 reaction equation
[CH2:1]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH2:5][CH2:4][N:3]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:2]12.[ClH:17].CN(C)CCCN=C=NCC.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:35]=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[NH2:34].C(N(C(C)C)CC)(C)C>ClCCl.Cl>[ClH:17].[ClH:17].[CH2:1]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([NH:34][C:33]2[CH:35]=[C:36]([O:40][CH3:41])[C:37]([O:38][CH3:39])=[C:31]([O:30][CH3:29])[CH:32]=2)=[O:12])[CH2:5][CH2:4][N:3]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:2]12

Participants

7

Reactant 4

HCID 322853,4,5-TrimethoxyanilineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22252364HCID 22252364, compound

Product 1

HCID 22252397HCID 22252397, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

1.2 g of the compound obtained in Step B, 1.05 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.92 g of 3,4,5-trimethoxyaniline in solution in 50 ml of dichloromethane and 1.75 ml of diisopropylethylamine are stirred, under argon, for 24 hours at room temperature. The reaction mixture is washed with 50 ml of water, decanted, dried over Na2SO4 and concentrated under a partial vacuum. The hydrochloride is then prepared in 20 ml of ethanol and 2 ml of an ethereal hydrogen chloride solution, enabling the expected product to be obtained.

Workup

  1. washThe reaction mixture is washed with 50 ml of water
  2. customdecanted
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under a partial vacuum
  5. customThe hydrochloride is then prepared in 20 ml of ethanol

Sources & evidence

ORD record
ord-e414df65c8b542f38f1bee4ce0f962a0
Source dataset
uspto-grants-2006_01
Patent number
US06992085B2

Reaction notes

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