Trifluoroacetic acid → N-(6-Amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

HRID 2069197Notes

Reaction equation

HRID 2069197 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[NH:13][C:12](=[O:20])[N:11]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:10]2=[O:26].FC(F)(F)C(O)=O>ClCCl.C(OCC)C>[NH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[NH:13][C:12](=[O:20])[N:11]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])[C:10]2=[O:26]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58964506N-[6-(2,4-dimethoxy-benzylamino)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

Product 1

HCID 11674068N-(6-Amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[6-(2,4-dimethoxy-benzylamino)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (725 mg, 1.56 mmol) in dichloromethane (4 ml) is added trifluoroacetic acid (0.5 ml) and the mixture is stirred at room temperature for 30 minutes. Then the solvent is removed by rotavapor evaporation to give an orange solid which is suspended in diethyl ether, filtered and the residue washed 3 times with diethyl ether and two times with ethyl acetate to give the title product as a pure orange solid, m.p. 326-335° C. (decomp.).

Workup

  1. customThen the solvent is removed by rotavapor evaporation
  2. customto give an orange solid which
  3. filtrationfiltered
  4. washthe residue washed 3 times with diethyl ether and two times with ethyl acetate

Sources & evidence

ORD record
ord-7eea605b2502417b98ad5e2a74b1f462
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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