Stannous Chloride → HCID 44140427, compound

HRID 1670681Notes

Reaction equation

HRID 1670681 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=1)[N:8]=[CH:7]2)([O-])=O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=1)[N:8]=[CH:7]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 578631566-Nitro-2-(1,3-benzodioxole-5-yl)-quinazoline

Product 1

HCID 44140427HCID 44140427, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6-nitro-2-(1,3-benzodioxol-5-yl)-quinazoline (37 g, 0.126 mol) and SnCl2 2H2O (117.2 g, 0.504 mol) in ethanol (500 ml) was heated at reflux for 1 h. After cooling to r. t., the solvent was removed i.v., chloroform was added and the mixture was basified with ammonia. The precipitate was filtered off and washed with chloroform. The filtrates were collected, washed with water and dried over Na2SO4. The solution was concentrated i.v., and the residue triturated with diisopropyl ether/petroleum ether. The solid was filtered and dried i.v. to give the titled product (21.2 g, 64% yield). C15H11N3O2, MW: 265.27. mp 191-192° C.; 1H NMR (DMSO-d6) 9.24 (s, 1H), 8.05 (dd, 1H), 7.91 (d, 1H), 7.73 (d, 1H), 7.39 (dd, 1H), 7.03 (d, 1H), 6.90 (d, 1H), 6.11 (s, 2H), 5.93 (s, 2H); IR (KBr) 3319, 3203, 1631, 1500, 1446; TLC (CHCl3/MeOH 9/1) Rf=0.3.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. custom, the solvent was removed i.v
  5. addition, chloroform was added
  6. filtrationThe precipitate was filtered off
  7. washwashed with chloroform
  8. customThe filtrates were collected
  9. washwashed with water
  10. dry with materialdried over Na2SO4
  11. concentrationThe solution was concentrated i.v
  12. custom, and the residue triturated with diisopropyl ether/petroleum ether
  13. filtrationThe solid was filtered
  14. customdried i.v

Sources & evidence

ORD record
ord-e4cd81fd52d64552ac31b8465d76d886
Source dataset
uspto-grants-2011_08
Patent number
US07994181B2

Reaction notes

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