N-(6-nitro-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide → N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

HRID 2069268Notes

Reaction equation

HRID 2069268 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[C:14]([F:17])([F:16])[F:15])[NH:10][C:9](=[O:18])[N:8]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:7]2=[O:24])([O-])=O>C(O)C.C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[C:14]([F:16])([F:15])[F:17])[NH:10][C:9](=[O:18])[N:8]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:7]2=[O:24]

Participants

5

Reactant 1

HCID 11964603N-(6-nitro-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11964604N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamideYield 61%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Procedure

A solution of 109 mg of N-(6-nitro-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide in 3 ml of ethanol and 3 ml of acetic acid is hydrogenated in the presence of 30 mg of 10% palladium on carbon. After disappearance of the starting material followed by TLC the reaction mixture is diluted with ethanol and acetic acid and slightly warmed up. The catalyst is filtered off and the filtrate concentrated to dryness. Trituration of the residue with ethyl acetate gives 61 mg (61%) of N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide as a yellow powder, m.p. 240° C. (decomp.). 1H-NMR (DMSO-d6, 400 MHz): 3.12 (s, 3H); 5.66 (s, 2H); 7.24 (s, 1H); 7.46 (s, 1H); 10.3 (br s, 1H); 11.4 (br s, 1H).

Workup

  1. temperatureslightly warmed up
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-4ffee2f310094415a6998cb51c76714e
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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