Thionyl Chloride → 3-(2-Chloroethyl)quinazolin-4(3H)-one

HRID 520278Notes

Reaction equation

HRID 520278 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9]1>O>[Cl:3][CH2:6][CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12943120HCID 12943120, compound

Product 1

HCID 45187433-(2-Chloroethyl)quinazolin-4(3H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

This thionyl chloride (1,095 mL, 15 mmol) was added to 3-(2-hydroxyethyl)quinazoline-4 (3H)-one (2.0 g, 10.52 mmol) in a reactor, forming a white suspension that heated spontaneously to 85° C. The reaction medium was kept at this temperature under agitation for thirty minutes, after which it was left to cool to about 40° C. Next, 50 mL of water was added, forming a pinkish suspension, which was kept under agitation for two hours. The product was then vacuum filtered and washed with three portions of 10 mL of an ethanol/water mixture (50% v/v), yielding 3-(2-chloroethyl) quinazoline-4 (3H)-one as a pale white solid (1.8 g, 8.63 mmol, yield=82%).

Workup

  1. customforming a white suspension
  2. waitThe reaction medium was kept at this temperature under agitation for thirty minutes
  3. waitafter which it was left
  4. temperatureto cool to about 40° C
  5. customforming a pinkish suspension, which
  6. filtrationvacuum filtered
  7. washwashed with three portions of 10 mL of an ethanol/water mixture (50% v/v)

Sources & evidence

ORD record
ord-4c663eee69d540ffb2f679782993721e
Source dataset
uspto-grants-2016_05
Patent number
US09326984B2

Reaction notes

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