Hydrochloric Acid → HCID 66748269, compound

HRID 2402016Notes

Reaction equation

HRID 2402016 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[S:10][C:11]=2[C:12]([O:14]CC)=[O:13])=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[S:10][C:11]=2[C:12]([OH:14])=[O:13])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66747606HCID 66747606, compound

Product 1

HCID 66748269HCID 66748269, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazole-5-carboxylate (12.8 g, 35.7 mmol) in THF (200 mL) and water (100 mL) was added 1.0 M LiOH (46.4 mL, 46.4 mmol) and the resulting solution was stirred at room temperature overnight. The mixture was acidified to pH 4 with 1 N HCl. The precipitated solids were filtered, washed with water and dried to give 11 g of the title compound as an a white solid. (93% yield). LC/MS (FA) ES+ 331. 1H NMR (400 MHz, d6-DMSO) δ: 13.86 (br s, 1H), 8.72-8.71 (m, 2H), 7.89-7.87 (m, 2H), 7.36-7.29 (m, 4H), 4.50 (s, 2H).

Workup

  1. filtrationThe precipitated solids were filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-51800ee3166c4af894f08fe86aa08fb5
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

Loading…