Phosphorus pentachloride → 4-Chloro-2-(1-methyl-5-nitro-1H-imidazol-2-yl)quinazoline

HRID 973209Notes

Reaction equation

HRID 973209 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[C:10]1[NH:19][C:18](=O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:22]>P(Cl)(Cl)(Cl)=O>[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[C:10]1[N:19]=[C:18]([Cl:22])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 1357273912-(1-Methyl-5-nitro-1H-imidazol-2-yl)quinazolin-4(1H)-one

Product 1

HCID 214020964-Chloro-2-(1-methyl-5-nitro-1H-imidazol-2-yl)quinazoline

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A suspension of 25 g of 2-(1-methyl-5-nitro-2-imidazolyl)-4-quinazolinone and 26.2 g of phosphorus pentachloride in 150 ml of phosphorus oxychloride is boiled for 3 hours and then evaporated in vacuo (12 Torr). The residue is taken up in methylene chloride and stirred with water for one hour at room temperature. The mixture is made alkaline with sodium bicarbonate and extracted by dropwise addition of methylene chloride. The mixture is dried with magnesium sulphate and treated with animal charcoal, filtered and evaporated in vacuo (12 Torr) at 30° C. The residue is mixed with ether, filtered and washed pure with ether to obtain the heading compound, m.p. 178°-181° C.

Workup

  1. customevaporated in vacuo (12 Torr)
  2. extractionextracted by dropwise addition of methylene chloride
  3. dry with materialThe mixture is dried with magnesium sulphate
  4. additiontreated with animal charcoal
  5. filtrationfiltered
  6. customevaporated in vacuo (12 Torr) at 30° C
  7. additionThe residue is mixed with ether
  8. filtrationfiltered
  9. washwashed pure with ether
  10. customto obtain the heading compound, m.p. 178°-181° C.

Sources & evidence

ORD record
ord-62279d4f02cf488fb8b4a6ae26723e95
Source dataset
uspto-grants-1977_10
Patent number
US04055642

Reaction notes

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