Benzenesulfonic Acid → HCID 86680482, compound

HRID 2406443Notes

Reaction equation

HRID 2406443 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[C:22]1([S:28]([OH:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[C:22]1([S:28]([OH:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 715443511429329-63-4

Product 1

HCID 86680482HCID 86680482, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethanol (2 g, 6.6 mmol) in ethanol (60 mL) was added benzenesulfonic acid (1.05 g, 6.6 mmol) slowly at 0° C., and then the mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated, the solid obtained was washed with hexane (10 mL) to afford 4-(1-(1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethanol benzenesulfonic acid salt as off-white solid (1.3 g, 43% yield), HPLC purity 99.6%, mp 165-167° C. 1H NMR (400 MHz, DMSO-d6): 8.81 (d, 2H), 8.04 (d, 2H), 7.93-7.89 (m, 3H), 7.57 (d, 2H), 7.33-7.28 (m, 5H), 7.09 (br s, 1H), 2.00 (s, 3H); LC-MS m/z calculated for [M+H]+ 301.07, found 301.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe solid obtained
  3. washwas washed with hexane (10 mL)

Sources & evidence

ORD record
ord-51c4e08794fd47d5a80723431d5468ad
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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