Sulfanilic acid → 4-(6-Chloro-4-quinazolinylamino)benzenesulphonic acid

HRID 235657Notes

Reaction equation

HRID 235657 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[S:13]([OH:23])(=[O:22])([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=[O:14]>C(O)C>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[NH:21][C:18]1[CH:19]=[CH:20][C:15]([S:13]([OH:23])(=[O:14])=[O:22])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8479Sulfanilic acidHCID 2460244,6-Dichloroquinazoline

Product 1

HCID 135372094-(6-Chloro-4-quinazolinylamino)benzenesulphonic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,6-Dichloroquinazoline (5.9 g, 0.03 mole) was added portionwise to sulphanilic acid (5.2 g, 0.03 mole) in 50% aqueous ethanol (200 ml) at 90° C. with stirring. The mixture was refluxed for 2 hours, cooled and filtered. The solid was washed with 50% aqueous ethanol and dried in an oven to give the title compound (9.2 g) as the hemihydrate m.p. greater than 300° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe solid was washed with 50% aqueous ethanol
  5. customdried in an oven

Sources & evidence

ORD record
ord-cc34361490594b21a045245fd81b2432
Source dataset
uspto-grants-1987_02
Patent number
US04640920

Reaction notes

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