Hydrochloric Acid → HCID 86588983, compound

HRID 656267Notes

Reaction equation

HRID 656267 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]([F:16])[C:4]=1[F:17])#[N:2].[ClH:18]>CO.CCOCC.[Pd]>[ClH:18].[F:17][C:4]1[C:5]([F:16])=[C:6]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[C:7]([F:10])=[C:8]([F:9])[C:3]=1[CH2:1][NH2:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 85810749HCID 85810749, compound

Product 1

HCID 86588983HCID 86588983, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4-cyano-2,3,5,6-tetrafluoro-1-methanesulfonylaminobenzene (11 mg) prepared in Step 1 was dissolved in methanol (5 ml) and to the solution were added a catalytic amount of 10% palladium/carbon and concentrated hydrochloric acid (300 μl), followed by stirring at room temperature under hydrogen gas atmosphere for 1 hour. The resulting mixture was diluted in ether, filtered through celite, concentrated under reduced pressure, and then washed with ethyl acetate to yield 2,3,5,6-tetrafluoro-4-methanesulfonylaminobenzylamine hydrochloride (7.0 mg, 59%).

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated under reduced pressure
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-0b561ad70b1d483cb7a3b7b64bf406c2
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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