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

HRID 1894069Notes

Reaction equation

HRID 1894069 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[N:17]=[C:18]=[O:19].[CH3:21][S:22]([NH:25][NH2:26])(=[O:24])=[O:23].[OH-].[Na+].Cl>C1COCC1>[N+:10]([C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][C:7]=1[C:13]([F:16])([F:15])[F:14])[NH:17][C:18](=[O:19])[N:26]([NH:25][S:22]([CH3:21])(=[O:24])=[O:23])[C:3]2=[O:2])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 269268MethanesulfonohydrazideHCID 11964606HCID 11964606, compound

Product 1

HCID 11964603N-(6-nitro-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamideYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2-isocyanato-5-nitro-4-trifluoromethyl-benzoic acid methyl ester (110 mg, 0.379 mmol) in dry THF (1.7 mL) was added a solution of CH3SO2NHNH2 (41.7 mg, 0.379 mmol) in dry THF (0.6 mL) at r.t. The resultant mixture turned into a white suspension that was stirred for one hour. A 1 M aq NaOH solution (0.379 mL) was added and stirring of the clear solution was continued for 4 h. After addition of 2 M HCl solution (0.472 mL) and evaporation of the THF, the precipitate was filtered and dried at 50° C./0.1 mm yielding N-(6-nitro-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (114 mg, 81%) as a slightly yellow powder, m.p. 220-232° C. (decomp.). 1H-NMR (DMSO-d6, 400 MHz): 3.15 (s, 3H), 7.66 (s, 1H), 8.62 (s, 1H), 10.50 (s, 1H), 12.41 (s, 1H).

Workup

  1. stirringstirring of the clear solution
  2. waitwas continued for 4 h
  3. filtrationthe precipitate was filtered
  4. customdried at 50° C./0.1 mm

Sources & evidence

ORD record
ord-622248e04d1549e480000585b172590b
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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