Phosphorus oxychloride → 2-Chloro-4-(2-chlorophenyl)-6-nitroquinazoline

HRID 1719510Notes

Reaction equation

HRID 1719510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=2)[NH:11][C:10](=O)[N:9]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:10]1[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=2)[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13245455HCID 13245455, compound

Product 1

HCID 132454562-Chloro-4-(2-chlorophenyl)-6-nitroquinazoline

Procedure

A mixture of 40 g of 4-(2-chloro phenyl) 6-nitro 2-quinazolone are 600 ml of phosphorus oxychloride is heated to reflux for 4 hours. The phosphorus oxychloride is evaporated in vacuo to dryness, then the residue is poured into an ice-water mixture. It is rendered alkaline with a 10% sodium hydroxide solution. The precipitate is drained and washed with acetonitrile. The product is purified by chromatography over a column of silica. By eluting with a chloroform-methanol (95-5 vol/vol) mixture, the expected product is isolated. Weight: 27 g; m.p.: 228° C. (isopropanol).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 hours
  3. customThe phosphorus oxychloride is evaporated in vacuo to dryness
  4. additionthe residue is poured into an ice-water mixture
  5. washwashed with acetonitrile
  6. customThe product is purified by chromatography over a column of silica
  7. washBy eluting with a chloroform-methanol (95-5 vol/vol) mixture

Sources & evidence

ORD record
ord-cca4daa209d948da9eff0ce428fab06e
Source dataset
uspto-grants-1985_09
Patent number
US04540696

Reaction notes

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