Ammonia → HCID 69337624, compound

HRID 2069305Notes

Reaction equation

HRID 2069305 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([N+:20]([O-])=O)=[CH:12][C:3]=1[C:4]([N:6]([S:8]([CH3:11])(=[O:10])=[O:9])[NH2:7])=[O:5].O.O.[Sn](Cl)Cl.N>Cl>[NH2:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[C:13]([NH2:20])=[CH:12][C:3]=1[C:4]([N:6]([S:8]([CH3:11])(=[O:10])=[O:9])[NH2:7])=[O:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 61436Stannous chloride dihydrateHCID 69338605HCID 69338605, compound

Product 1

HCID 69337624HCID 69337624, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 80 mg (0.23 mmol) of N-(2-amino-5-nitro-4-trifluoromethyl-benzoyl)-methanesulfonhydrazide in 1.5 ml of conc. hydrochloric acid, 270 mg (1.17 mmol) of tin(II) chloride dihydrate is added and the mixture is stirred at room temperature for 20 min. The mixture is neutralized at 0° C. with an aqueous solution of ammonia. The product is extracted with ethyl acetate. The combined organic fractions are dried, evaporated and purified by flash-master chromatography (0-70% gradient cyclohexane/ethyl acetate) to yield N-(2,5-diamino-4-trifluoromethyl-benzoyl)-methanesulfonhydrazide as hydrochloride salt. M.p. 220.8 -225.5° C.; 1H-NMR ; DMSO-d6 (400 MHz, ppm): 6.98 (s, 1H, aromatic); 6.88 (s, 1H, aromatic); 2.98 (s, 3H, S02-CH3). LC-MS: 313 [M+H]+; Agilent LCIMSD 1100 Series; LC-MS method: Column: SunFireC 18, 4.6*50 mm, 3.5 μm; positive MS; water/acetonitril 95:5 to 5:95 in 5 min, flow: 1.5 ml/min.

Workup

  1. extractionThe product is extracted with ethyl acetate
  2. customThe combined organic fractions are dried
  3. customevaporated
  4. custompurified by flash-master chromatography (0-70% gradient cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-e67b1a4769844abeb25be1fd56ec0a3d
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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