Nitrilooxonium tetrafluoroborate → 2-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-3-trifluoromethyl-benzoic acid

HRID 583333Notes

Reaction equation

HRID 583333 reaction equation
[CH2:1]([N:8]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](N)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.N#[O+:39]>CC#N>[CH2:1]([N:8]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:39])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 213109172-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-3-trifluoromethyl-benzamide

Product 1

HCID 213109182-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-3-trifluoromethyl-benzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 0.192 g (0.41 mmol) of the product of Example 123 in 2.5 mL of dry CH3CN was added 0.068 g(0.58 mmol) of nitrosonium tetrafluoroborate. The resulting mixture was stirred for 1 h and then added 0.040 g(0.34 mmol) of the same reagent and stirred for additional 1 h. The reaction was quenched with water and filtered to provide 0.141 g (74%) of the desired carboxylic acid as a white solid. Electrospray Mass Spec 466.2(M+H).

Workup

  1. stirringstirred for additional 1 h
  2. customThe reaction was quenched with water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f20e5b1405724a6aa27be179a413016a
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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