Water → HCID 12318784, compound

HRID 1601650Notes

Reaction equation

HRID 1601650 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[C:12]1([N:18]=[C:19]=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)O.O>CN1CCCC1=O>[C:12]1([N:18]2[C:6](=[O:8])[C:5]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[NH:11][C:19]2=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7672Phenyl isocyanateHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 12318784HCID 12318784, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

42.5 g of 4-chloroanthranilic acid were dissolved in 250 ml of N-methylpyrrolidone and 29.5 g of phenyl isocyanate were added dropwise at room temperature in 30 minutes. The mixture was further stirred for 5 hours at 80° C. and then 24.5 g of concentrated sulphuric acid were added dropwise in the course of 1 hour. The mixture was then further stirred at 80° C. for 3 hours, then cooled to room temperature, 500 ml of water were added, the product precipitated out was filtered off by suction, washed with water and dried in a vacuum drying cabinet. In this manner 57.4 g (85% of theory) of pure 3-phenyl-7-chloro-quinazoline-2,4-dione were obtained having a melting point of above 300° C.

Workup

  1. stirringThe mixture was then further stirred at 80° C. for 3 hours
  2. temperaturecooled to room temperature
  3. customthe product precipitated out
  4. filtrationwas filtered off by suction
  5. washwashed with water
  6. customdried in a vacuum
  7. customdrying cabinet

Sources & evidence

ORD record
ord-26b27a73203049be87ec8845e75bb07c
Source dataset
uspto-grants-1999_11
Patent number
US05977362

Reaction notes

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