Stannous Chloride → N'-(8-aminoquinazolin-4-yl)-4-methylbenzene-1-sulfonohydrazide

HRID 513744Notes

Reaction equation

HRID 513744 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][NH:12][C:13]2[C:22]3[C:17](=[C:18]([N+:23]([O-])=O)[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][N:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[Sn]Cl>Cl.CCO>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[N:16]=[CH:15][N:14]=[C:13]2[NH:12][NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 114625144-Methyl-N'-(8-nitroquinazolin-4-yl)benzene-1-sulfonohydrazide

Product 1

HCID 68183283N'-(8-aminoquinazolin-4-yl)-4-methylbenzene-1-sulfonohydrazideYield 67.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 2 general procedure 4, 4-methyl-N′-(8-nitroquinazolin-4-yl)benzene-1-sulfonohydrazide 478 (100 mg, 0.27 mmol), SnCl2 (310 mg, 1.67 mmol), 6N HCl (1 drop) and EtOH (3 ml) at 80° C. for 3 h gave the title compound (60 mg, 65%) which was used in the next step without further purification.

Workup

  1. customat 80° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-ca9f7d2fad424edeb9ae2685fda89bfd
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…