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Hydrochloric Acid → 2-(2-(3-(Trifluoromethyl)phenylsulfonyl)ethylthio)nicotinic acid

HRID 660052
Notes
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Reaction equation

HRID 660052 reaction equation
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].Cl[CH2:18][CH2:19][S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1)(=[O:22])=[O:21].Cl>CN(C=O)C.C(OCC)(=O)C.O>[F:32][C:29]([F:30])([F:31])[C:25]1[CH:24]=[C:23]([S:20]([CH2:19][CH2:18][S:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])(=[O:21])=[O:22])[CH:28]=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27365062-Chloroethyl-[3-(trifluoromethyl)phenyl]sulphoneHCID 178524460HCID 178524460, compound

Product 1

HCID 28213922-(2-(3-(Trifluoromethyl)phenylsulfonyl)ethylthio)nicotinic acidYield 88.4%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

683 mg (4.92 mmol) of K2CO3 were added to a suspension of 349 mg (2.25 mmol) of 2-mercaptonicotinic acid in DMF (5 ml), and the mixture was stirred for 30 min at RT. 614 mg (2.25 mmol) of 2-chloroethyl-(3-(trifluoromethyl)phenyl)sulfone were then added, and stirring was continued for a further 72 h at RT. The reaction solution was concentrated in vacuo, the residue obtained was taken up in ethyl acetate, and water was added. The pH was adjusted to 3 with 2 M hydrochloric acid, and the phases were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. 778 mg (1.99 mmol, 88%) of 2-(2-(3-(trifluoromethyl)phenylsulfonyl)ethylthio)nicotinic acid were obtained as residue.

Workup

  1. stirringstirring
  2. waitwas continued for a further 72 h at RT
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customthe residue obtained
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d01fe1f38a9343b5b7ab2a489df79fba
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084470B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes