HCID 19990444, compound → HCID 19990456, compound

HRID 346163Notes

Reaction equation

HRID 346163 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([S:19]([NH:22][C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:24])(=[O:21])=[O:20])=[CH:11][C:10]=1[N+:30]([O-])=[O:31])([C:3]([O:5]CC)=O)=[O:2]>CN(C)C=O.[Pt]>[C:23]([NH:22][S:19]([C:12]1[CH:11]=[C:10]2[C:9]([NH:8][C:1](=[O:2])[C:3](=[O:5])[N:30]2[OH:31])=[CH:14][C:13]=1[C:15]([F:16])([F:18])[F:17])(=[O:20])=[O:21])([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:24]

Participants

4

Reactant 1

HCID 19990444HCID 19990444, compound

Product 1

HCID 19990456HCID 19990456, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-ethoxalylamino-4-ethoxalylaminosulfonyl-2-nitro-5-trifluoromethylbenzene (24.6 g, 50 mmol) in 200 ml of N,N-dimethylformamide was hydrogenated at room temperature and atmospheric pressure in the presence of 1 g of 5% platinum on carbon for 2 h. The catalyst was filtered off and washed with N,N-dimethylformamide. The filtrate was evaporated to dryness and the gummy residue was refluxed with 100 ml of ethanol for about 20 min. The mixture was cooled and the precipitated product was collected by filtration and washed with ethanol and ether to give 12.7 g (59%) of the title compound. M.p. 222° C. decomp. (DSC); IR (KBr): 1685 cm-1 ; 1H-NMR (DMSO-d6): 1.25 (t,J=7Hz, 3H, CH3), 4.23 (q,J=7Hz, 2H, CH2), 7.67 (s, 1H, ArH), 8.30 (s, 1H, ArH), 10.8 (broad s, 2H, exchangeable), 12.5 (broad s, 1H, exchangeable).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with N,N-dimethylformamide
  4. customThe filtrate was evaporated to dryness
  5. temperaturethe gummy residue was refluxed with 100 ml of ethanol for about 20 min
  6. temperatureThe mixture was cooled
  7. filtrationthe precipitated product was collected by filtration
  8. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-bbbf132ce45c4884a7ce3f0858a285b0
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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