Nitric Acid → HCID 86680484, compound

HRID 2406445Notes

Reaction equation

HRID 2406445 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.[N+:22]([O-:25])([OH:24])=[O:23]>C(O)C.C(O)(C)C>[N+:22]([O-:25])([O-:24])=[O:23].[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][NH+:19]=[CH:20][CH:21]=3)([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 715443511429329-63-4

Product 1

HCID 86680484HCID 86680484, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethanol (2 g, 10 mmol) in ethanol (6 mL) and isopropyl alcohol (30 mL) was cooled to 0° C., and to this mixture was added 6N HNO3 (6 mL) in 30 mL of isopropyl alcohol. The reaction mixture was stirred for 1 hour at room temperature. The solid formed was filtered and washed with hexane (10 mL) to afford 4-(1-(2-(4-fluorophenyl)thiazol-5-yl)-1-hydroxyethyl)pyridin-1-ium nitrate as an off-white solid (2.3 g, 63% yield), HPLC purity 99.8%, mp 188-191° C. 1H NMR (400 MHz, DMSO-d6): 8.85 (d, 2H), 8.10 (d, 2H), 7.92 (t, 3H), 7.30 (t, 2H), 7.13 (br s, 1H), 2.01 (s, 3H); LC-MS m/z calculated for [M+H]+ 301.07, found 301.1.

Workup

  1. customThe solid formed
  2. filtrationwas filtered
  3. washwashed with hexane (10 mL)

Sources & evidence

ORD record
ord-910c9bc4a0f842fca67d6b082de78136
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

Loading…