2,4-Dimethoxybenzoic acid → HCID 19040985, compound

HRID 2399947Notes

Reaction equation

HRID 2399947 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH:14]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])[CH3:15].OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:17]([CH:14]([CH3:16])[CH3:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7]

Participants

6

Reactant 4

HCID 70522,4-Dimethoxybenzoic acidHCID 13032N-IsopropylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 19040985HCID 19040985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2,4-dimethoxybenzoic acid (4.31 g, 23.7 mmol) in 35 mL of dichloromethane is treated with N-isopropylaniline (3.07 mL, 21.33 mmol), hydroxybenzotriazole (3.2 g, 23.7 mmol), and 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (4.54 g, 23.7 mmol). This solution is stirred at room temperature for 18 hours and the resulting solution is partitioned between ethyl acetate and 1N hydrochloride solution. The organic layer is washed with water, dried over sodium sulfate and concentrated. The resulting material is purified by chromatography on silica gel (150 g) with 40-60% ethyl acetate/hexane as the eluent to afford 2,4-dimethoxy-N-(1-methylethyl)-N-phenylbenzamide as a colorless foam.

Workup

  1. customthe resulting solution is partitioned between ethyl acetate and 1N hydrochloride solution
  2. washThe organic layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting material is purified by chromatography on silica gel (150 g) with 40-60% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-2623c8935b6b43a6adb1dd4b8de9f75b
Source dataset
uspto-grants-1995_09
Patent number
US05451700

Reaction notes

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