N,N-Dimethylaniline → HCID 178517815, compound

HRID 1702978Notes

Reaction equation

HRID 1702978 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[NH:3][C:2]1=O.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:2]1[N:3]=[C:4]([OH:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 64048Quinazolinedione

Product 1

HCID 178517815HCID 178517815, compound

Procedure

A mixture of 300 g of the product of Step A, 150 ml of N,N-dimethyl-aniline and 1 liter of phosphoryl chloride was refluxed for 51/2 hours and was cooled and poured with vigorous stirring onto crushed ice. The mixture was filtered and the product was washed with ice water until the wash water was neutral. The product was added with stirring to 2.25 liters of 2 N aqueous sodium hydroxide and the mixture was stirred for about 3 hours until complete dissolution occured. The mixture was filtered and the filtrate was neutralized by addition of glacial acetic acid. The mixture was filtered and the product was washed with water and dried to obtain 263 g of 2-chloro-4-hydroxy-quinazoline.

Workup

  1. temperaturewas refluxed for 51/2 hours
  2. temperaturewas cooled
  3. additionpoured
  4. customonto crushed ice
  5. filtrationThe mixture was filtered
  6. washthe product was washed with ice water until the wash water
  7. additionThe product was added
  8. stirringwith stirring to 2.25 liters of 2 N aqueous sodium hydroxide
  9. stirringthe mixture was stirred for about 3 hours until complete dissolution
  10. filtrationThe mixture was filtered
  11. additionthe filtrate was neutralized by addition of glacial acetic acid
  12. filtrationThe mixture was filtered
  13. washthe product was washed with water
  14. customdried

Sources & evidence

ORD record
ord-b0ee6bddf6da456eb3ac72964c3597e6
Source dataset
uspto-grants-1982_09
Patent number
US04350695

Reaction notes

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