Chloroform → 3-(2-Chloroethyl)-2-ethyl-3,4-dihydro-4-quinazolinone

HRID 1754126Notes

Reaction equation

HRID 1754126 reaction equation
[CH2:1]([C:3]1[N:12]([CH2:13][CH2:14]O)[C:11](=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].S(Cl)([Cl:19])=O.C(Cl)(Cl)Cl>CCCCCC>[Cl:19][CH2:14][CH2:13][N:12]1[C:11](=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 103760834(3H)-Quinazolinone, 2-ethyl-3-(2-hydroxyethyl)-

Product 1

HCID 597239043-(2-Chloroethyl)-2-ethyl-3,4-dihydro-4-quinazolinoneYield 32.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2-ethyl-3-(2-hydroxyethyl)quinazoline-4(3H)-one (5.00 g; 22.91 mmol) and thionyl chloride (1.672 mL, 22.91 mmol) were added to a 150 mL reactor, together with 60 mL of chloroform. The reaction medium was heated to reflux and for completing the reaction, which was accompanied through CG/MS. After the end of the reaction, 100 mL of hexane were added and the solution was agitated at room temperature in order to precipitate the product. The resulting suspension was vacuum filtered, washed with two portions of hexane and dried, yielding 3-(2-chloroethyl)-2-ethylquinazoline-4(3H)-one as a white solid (1.78 g; 7.52 mmol; yield: 32.8%).

Workup

  1. temperatureThe reaction medium was heated
  2. temperatureto reflux
  3. customthe reaction, which
  4. additionwere added
  5. customto precipitate the product
  6. filtrationfiltered
  7. washwashed with two portions of hexane
  8. customdried

Sources & evidence

ORD record
ord-72efc72f5b424f1cb48cf501b41b280d
Source dataset
uspto-grants-2015_10
Patent number
US09169218B2

Reaction notes

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