Phosphorus oxychloride → 7-(Benzylthio)-4-chloroquinazoline

HRID 1473682Notes

Reaction equation

HRID 1473682 reaction equation
[CH2:1]([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:22].CCN(C(C)C)C(C)C>ClCCCl>[CH2:1]([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:22])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1364090647-(benzylthio)quinazolin-4(3H)-one

Product 1

HCID 866877657-(Benzylthio)-4-chloroquinazoline

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A flask was charged with 7-(benzylthio)quinazolin-4(3H)-one (5.0 g, 18.63 mmol) and DCE (93 ml). POCl3 (5.21 ml, 55.9 mmol) was added, followed by Hunig's base (16.27 ml, 93 mmol). The flask was fitted with a reflux condensor, and the reaction was for two hours at 90° C. The reaction was washed with water and the layers were separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-75% EtOAc:Heptane) to afford 7-(benzylthio)-4-chloroquinazoline as a light yellow solid. (ESI) 287.0 (M+H)+.

Workup

  1. customThe flask was fitted with a reflux condensor
  2. washThe reaction was washed with water
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-75% EtOAc:Heptane)

Sources & evidence

ORD record
ord-98221bc1417747be810755add727dbe7
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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