Water → 6-(2-Naphthalenylsulfonyl)-2,4-quinazolinediamine

HRID 52631Notes

Reaction equation

HRID 52631 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:13][C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)[CH:8]=2)[N:3]=1.[Mn]([O-])(=O)(=O)=[O:25].[K+].[OH2:30]>C(O)(=O)C>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:13]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)(=[O:25])=[O:30])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 39762842,4-Quinazolinediamine, 6-(2-naphthalenylthio)-

Product 1

HCID 986526-(2-Naphthalenylsulfonyl)-2,4-quinazolinediamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.0 grams (0.006 mole) of 2,4-diamino-6-(naphth-2-ylthio)quinazoline (prepared in Example 7) in 80 mL of acetic acid was stirred, and a solution of 2.0 grams (0.013 mole) of potassium permanganate in 75 mL of water was added dropwise during a 1 hour period. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. After this time, the reaction mixture was filtered through diatomaceous earth. The filtrate was made basic by adding an excess amount of concentrated ammonium hydroxide. The resultant precipitate was collected by filtration and was washed in turn with water, methanol, and acetone. The precipitate was stirred in hot N,N-dimethylformamide and treated with decolorizing carbon. The mixture was filtered hot, and the filtrate was set aside. The residue collected by the filtration was again stirred with hot N,N-dimethylformamide and filtered. The two filtrates were combined and poured into 500 grams of ice. The resultant solid was collected by filtration, yielding 0.9 gram of 2,4-diamino-6-(naphth-2-ylsulfonyl)quinazoline, mp 300°-302° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. filtrationAfter this time, the reaction mixture was filtered through diatomaceous earth
  3. additionby adding an excess amount of concentrated ammonium hydroxide
  4. filtrationThe resultant precipitate was collected by filtration
  5. washwas washed in turn with water, methanol, and acetone
  6. stirringThe precipitate was stirred in hot N,N-dimethylformamide
  7. additiontreated with decolorizing carbon
  8. filtrationThe mixture was filtered hot
  9. filtrationThe residue collected by the filtration
  10. stirringwas again stirred with hot N,N-dimethylformamide
  11. filtrationfiltered
  12. additionpoured into 500 grams of ice
  13. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-b76b2e9701924d93ab5d86224c6cb0ae
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Reaction notes

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