Acetic Acid → HCID 67133585, compound

HRID 1925544Notes

Reaction equation

HRID 1925544 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].Br[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1.C(O)(=O)C>CN(C=O)C.O.CC(=O)OCC.CC(=O)OCC.CCCCCC>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][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])=[CH:22][CH:23]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 147371331-(3-Bromopropyl)-4-fluorobenzeneHCID 178524460HCID 178524460, compound

Product 1

HCID 67133585HCID 67133585, compoundYield 47%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4.9 g (35.8 mmol) of K2CO3 were added to a solution of 2.5 g (16.3 mmol) of 2-mercapto-nicotinic acid in DMF (40 ml), and the mixture was stirred for 30 min at RT. 3.5 g (16.3 mmol) of 1-(3-bromopropyl)-4-fluorobenzene were then added and stirring was carried out for a further 72 h at RT. The mixture was then diluted with water and EA and adjusted to pH 5-6 with 5M acetic acid. The organic phase was separated off, washed with water, dried over MgSO4, filtered and concentrated in vacuo. CC (EA/hexane 1:2→5:1) of the residue yielded 2.2 g (7.6 mmol, 47%) of 2-(3-(4-fluoro-phenyl)propylthio)nicotinic acid.

Workup

  1. stirringstirring
  2. waitwas carried out for a further 72 h at RT
  3. customThe organic phase was separated off
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-778390705356493ba3a6afd7e98f336b
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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