Methyl 2-(3,4-dimethoxyphenyl)ethanimidate--hydrogen chloride (1/1) → Hydrochloric Acid

HRID 1595313Notes

Reaction equation

HRID 1595313 reaction equation
[ClH:1].CO[C:4](=[NH:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.N([C:24]1[C:37]([NH:38]C2C=CC=CC=2)=[CH:36][CH:35]=[CH:34][C:25]=1[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])C1C=CC=CC=1>CO.C(OCC)C>[CH3:15][O:14][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[O:12][CH3:13])[CH2:5][C:4]1[NH:16][C:36]2[CH:35]=[CH:34][C:25]([C:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:27])=[CH:24][C:37]=2[N:38]=1.[ClH:1]

Participants

6

Reactant 2

HCID 24194687Methyl 2-(3,4-dimethoxyphenyl)ethanimidate--hydrogen chloride (1/1)HCID 86757354HCID 86757354, compound

Product 2

HCID 313Hydrochloric AcidHCID 178489866HCID 178489866, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl-(3,4dimethoxyphenyl)-acetimidate hydrochloride (2.5 g; 10 mmol) and 2,3-diamiinobenzophenone (2.1 g; 10 mmol) in methanol (70 mL) was stirred at ambient temperature for 72 hours. The reaction mixture was concentrated to dryness, and H2O was added. The solid (2.3 g) was subjected to flash chromatography on silica gel (CH2Cl2/MeOH; 9:1) to afford a gummy material. This was dissolved in diethyl ether, and Ether-HCl was added to obtain the title compound as a buff solid, hydrochloride, penta-hydrate (250 mg), m.p. 172-175° C. Anal. Calcd. for C23H20N2O3HCl.5H2O: C, 66.97; H, 5.23; N, 6.79. Found: C, 67.11, H, 4.84; N, 6.77. Mass Spectrum: (EI; M+) m/z 372. 1H-NMR (D)MSO-d6; 400 MHz) δ8.0 (s, 1H) 7.84-7.9 (m, 2H), 7.68-7.77 (m, 3H), 7.55-7.61 (m, 2H), 7.2 (s, 1H), 6.93-7.01 (m, 2H), 4.42 (s, 2H), 3.79 (s, 3H), 3.77 ppm (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness, and H2O
  2. additionwas added
  3. customto afford a gummy material

Sources & evidence

ORD record
ord-b597cee666cd4c199b0c13d8b3e81c33
Source dataset
uspto-grants-2001_09
Patent number
US06288100B1

Reaction notes

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