Hydrochloric Acid → HCID 56832762, compound

HRID 2401869Notes

Reaction equation

HRID 2401869 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[N:11]=[C:12]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[S:13][C:14]=2[C:15]([O:17]CC)=[O:16])[CH3:9])=[CH:4][CH:3]=1.O1CCCC1.CO.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[N:11]=[C:12]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[S:13][C:14]=2[C:15]([OH:17])=[O:16])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66749544HCID 66749544, compound

Product 1

HCID 56832762HCID 56832762, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 4-[1-(4-chlorophenyl)ethyl]-2-(morpholin-4-yl)-1,3-thiazole-5-carboxylate (1.42 g, 0.00373 mol) in tetrahydrofuran (30.2 mL, 0.373 mol) and methanol (6.04 mL, 0.149 mol) was added sodium hydroxide (1.0N in water, 29.8 mL, 0.0298 mol), and the resulting cloudy mixture was heated at 65° C. for 5 hours. The reaction was cooled to room temperature, diluted with water, and adjusted to pH 3.0 via addition of 1N aqueous HCl. The mixture was transferred to a separatory funnel and the layers separated. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford 4-[1-(4-chlorophenyl)ethyl]-2-(morpholin-4-yl)-1,3-thiazole-5-carboxylic acid (121) (1.21 g, yield 92%) as a white solid. LCMS: (FA) ES+ 353; 1H NMR (400 MHz, DMSO) δ 12.70 (bs, 1H), 7.37-7.34 (m, 2H), 7.33-7.30 (m, 2H), 5.09 (q, J=7.2, 1H), 3.69-3.76 (m, 4H), 3.48-3.39 (m, 4H), 1.49 (d, J=6.8, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe mixture was transferred to a separatory funnel
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d95a3b88c4f4ad8a077ae481e7f339a
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

Loading…