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Formic Acid → 5-(Trifluoromethyl)thiophene-2-sulfonamide

HRID 6974
Notes
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Reaction equation

HRID 6974 reaction equation
S(C1C=CC(N2C(O[C:17]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[S:19][C:18]=3[S:26]([NH2:29])(=[O:28])=[O:27])=NN=N2)=CC=1)(=O)(=O)N.O.CCO.C(O)=O>C1C=CC=CC=1.[Pd]>[F:25][C:22]([F:23])([F:24])[C:20]1[S:19][C:18]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:17][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 284Formic AcidHCID 702EthanolHCID 962WaterHCID 220194903-[1-(4-sulfamoyl-phenyl)-1H-tetrazol-5-yloxy]-5-trifluoromethyl-thiophene-2-sulfonamide

Product 1

HCID 220194975-(Trifluoromethyl)thiophene-2-sulfonamideYield 17%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 241BenzeneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 3-[1-(4-sulfamoyl-phenyl)-1H-tetrazol-5-yloxy]-5-trifluoromethyl-thiophene-2-sulfonamide (210 mg, 0.47 mmol) in benzene (50 mL) is added H2O (2 mL), EtOH (3 mL), formic acid (2 mL) and 10% palladium on carbon (350 mg). The mixture is heated to 80° C. overnight. The reaction mixture is cooled to room temperature and diluted with benzene (50 mL). The reaction mixture is filtered. The benzene layer is dried (Na2SO4), filtered and concentrated. The crude product is chromatographed on silica gel, eluting with EtOAc:Hex (1:10) to afford the title compound (18 mg, 17%) as a white solid.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe reaction mixture is filtered
  3. dry with materialThe benzene layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is chromatographed on silica gel
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-83b360ca114c47f9936ef07085d51598
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084170B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes