Pyridine → 2-(4-Isopropoxyphenoxy)-1,3-thiazole-5-carbaldehyde oxime

HRID 404865Notes

Reaction equation

HRID 404865 reaction equation
[CH:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[S:11][C:12]([CH:15]=O)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].N1C=CC=CC=1.Cl.[NH2:26][OH:27]>O>[CH:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[S:11][C:12]([CH:15]=[N:26][OH:27])=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 16110745HCID 16110745, compound

Product 1

HCID 861014162-(4-Isopropoxyphenoxy)-1,3-thiazole-5-carbaldehyde oximeYield 85.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of Example 1C (2.5 g, 0.0095 mol) in pyridine (15 mL, 0.19 mol) was added hydroxylamine hydrochloride (6.6 g, 0.095 mol) portion wise and the mixture was stirred at room temperature for 5 minutes and it solidified. The mixture was then heated at 70° C. for 0.5 hours. Water (300 mL) was added and the reaction was stirred for 20 minutes. The solid was filtered and air-dried to give 2.26 g of product as a white solid (85% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.28 (d, J=5.49 Hz, 6H) 4.54-4.68 (m, 1H) 7.00 (d, J=9.16 Hz, 2H) 7.28 (d, J=9.16 Hz, 2H) 7.68 (s, 1H) 7.77 (s, 1H) 11.89 (s, 1H). MS (ESI), m/z 279.0 (M+H)+.

Workup

  1. temperatureThe mixture was then heated at 70° C. for 0.5 hours
  2. stirringthe reaction was stirred for 20 minutes
  3. filtrationThe solid was filtered
  4. customair-dried

Sources & evidence

ORD record
ord-200eaf73a2e342669207ef3e44f42415
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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