N,N-Dimethylethylenediamine → HCID 13646103, compound

HRID 979503Notes

Reaction equation

HRID 979503 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]([NH:14][C:15]1[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:17]([OH:19])=O)=O.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][NH2:28]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]1[N:28]([CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])[C:17](=[O:19])[C:16]2[C:15](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 53760850HCID 53760850, compound

Product 1

HCID 13646103HCID 13646103, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 0.62 g (2 mmol) of N-(2,5-dimethoxyphenylacetyl) anthranilic acid and 0.36 g (3 mmol) of 2-dimethylaminoethylamine in xylene (5 ml) were heated under reflux for 24 hours. After cooling, the resulting reaction mixture was purified by silica gel column chromatography (eluent; chloroform: ethanol=98:2) to obtain 0.10 g (yield 14%) of 2-(2,5-dimethoxyphenylmethyl)-3-(2-dimethylaminoethyl)-4(3H) quinazolinone as an oily substance. 0.10 g of the oily substance thus obtained was dissolved in ethanol (1 ml) and then a 7% HCl-ethanol solution (0.2 mol) was added thereto and the resulting reaction mixture was cooled overnight. The resulting colorless precipitates were collected by filtration to obtain 0.1 g of the hydrochloride which is the desired compound. This hydrochloride coincides with the compound obtained in Example 16 in melting point and infrared absorption spectrum.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling
  4. customthe resulting reaction mixture
  5. customwas purified by silica gel column chromatography (eluent; chloroform: ethanol=98:2)

Sources & evidence

ORD record
ord-31cd944a4fa84dae87b3349c9605e9ff
Source dataset
uspto-grants-1987_05
Patent number
US04668682

Reaction notes

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