Acetic Acid → 3-Amino-8-bromo-n,n-diethyl-1,2-dihydro-1-oxobenzo[f]quinazolin-9-sulfonamide

HRID 2289250Notes

Reaction equation

HRID 2289250 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:18]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])(=[O:20])=[O:19])[C:15]([Br:17])=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1.C(O)(=O)C>C(OC(=O)C(C)(C)C)(=O)C(C)(C)C>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:18]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])(=[O:19])=[O:20])[C:15]([Br:17])=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 1358381053-Amino-8-bromo-N,N,-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonamide

Product 1

HCID 1358381543-Amino-8-bromo-n,n-diethyl-1,2-dihydro-1-oxobenzo[f]quinazolin-9-sulfonamideYield 33.2%

Reagents, catalysts & solvents 1

HCID 15234Pivalic anhydrideSolvent

Procedure

3-Amino-8-bromo-N,N,-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one- 9-sulfonamide (0.165 g,0.39 mmole) was suspended in pivalic anhydride (5 ml) (Aldrich) and heated under nitrogen until dissolved. The solution was heated under reflux for 10 minutes, cooled, and the pivalic anhydride removed in vacuo. The dried solid was dissolved in benzene (20 ml), pyridine (0.05 ml) added, and the solution heated to boiling under nitrogen. N-8romosuccinimide (0.07 g, 0.47 mmole) was added, and the mixture refluxed for an additional 6 hours. The reaction mixture was cooled to room temperature, solvent removed in vacuo, and the solid residue crystallized from methanol. The pivalamide (0.105 g) was dissolved in methanol(2 ml), IN NaOH(4 ml) added, and the solution heated to reflux under nitrogen for 1 hour. The cooled reaction mixture was neutralized with dilute acetic acid, the crystals collected by filtration and suspended in methanol. The collected crystals were dried in vacuo to give 3-amino-8-bromo-N,N- diethyl-1,2-dihydro-1-oxobenzo[f]quinazolin-9-sulfonamide (0.055 g, 33%). MD >250° C. 1H NMR (DMSO-d 200 MHz) δ: 1.10 (t, J=7 Hz, 6'6H, ethyl CH,), 3.38 (q, J=7 Hz, 4H, ethyl CH2), 6.78 (br s, 2H, NH2), 7.47 (d, J=9Hz, 1H, Ar), 8.09 (d, J=9Hz, 1H, Ar), 8.40 (s, IH, Ar), 10.30 (s, 1H, Ar), 11.32 (br s 1H, NH). Anal Calculated for C16H17BrN4 03S: C,45.19; H,4.03; Br,18.79; N,13.17; S,7.54. Found: C,45.10; H,4.03; Br,18.74; N,13.07; S,7.56.

Workup

  1. temperatureheated under nitrogen
  2. dissolutionuntil dissolved
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 10 minutes
  5. temperaturecooled
  6. customthe pivalic anhydride removed in vacuo
  7. dissolutionThe dried solid was dissolved in benzene (20 ml)
  8. additionpyridine (0.05 ml) added
  9. temperaturethe solution heated
  10. additionN-8romosuccinimide (0.07 g, 0.47 mmole) was added
  11. temperaturethe mixture refluxed for an additional 6 hours
  12. customsolvent removed in vacuo
  13. customthe solid residue crystallized from methanol
  14. dissolutionThe pivalamide (0.105 g) was dissolved in methanol(2 ml), IN NaOH(4 ml)
  15. additionadded
  16. temperaturethe solution heated
  17. temperatureto reflux under nitrogen for 1 hour
  18. customThe cooled reaction mixture
  19. filtrationthe crystals collected by filtration
  20. customThe collected crystals were dried in vacuo

Sources & evidence

ORD record
ord-72dac68ea7524ea694e7f32730e10dd2
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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