Ethanolamine → HCID 20200468, compound

HRID 979498Notes

Reaction equation

HRID 979498 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([NH:12][C:13]1[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:15]([OH:17])=O)=O.[CH2:22]([CH2:24][NH2:25])[OH:23]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]1[N:25]([CH2:24][CH2:22][OH:23])[C:15](=[O:17])[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 759761HCID 759761, compound

Product 1

HCID 20200468HCID 20200468, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 3.0 g (10 mmol) of methyl ester of N-(2-methoxyphenylacetyl)anthranilic acid and 1.2g (20 mmol) of monoethanolamine in xylene was heated at 180° C. for 16 hours in a sealed tube. After cooling, the precipitated crystals were collected by filtration to obtain 0.7 g (22%) of 2-(2-methoxyphenylmethyl)-3-(2-hydroxyethyl)- 4(3H)-quinazolinone (m.p.: 154°-155° C.). Subsequently, to 0.7 g (2.2 mmol) of this 3-(2-hydroxyethyl) derivative was added thionyl chloride (5 ml) and the resulting reaction mixture was stirred at room temperature for 1 hour. An excess of the thionyl chloride was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent:dichloromethane) to obtain 0.14 g (20%) of 2-(2-methoxyphenylmethyl)-3-(2-chloroethyl)-4(3H)-quinazolinone. (m.p.: 109°-111° C.).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-875d565f5c7c44b79dd45010ff34e712
Source dataset
uspto-grants-1987_05
Patent number
US04668682

Reaction notes

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