Water → HCID 86711940, compound

HRID 1475249Notes

Reaction equation

HRID 1475249 reaction equation
[NH:1]=[C:2]([NH:4][NH:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[N:12]=1)=O)[CH3:3].O>C(O)CO>[CH3:3][C:2]1[NH:4][N:5]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[N:12]=2)[N:1]=1

Participants

4

Reactant 2

HCID 962WaterHCID 178465664HCID 178465664, compound

Product 1

HCID 86711940HCID 86711940, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of N′-(1-iminoethyl)-4-(4-(trifluoromethoxy)phenyl)thiazole-2-carbohydrazide (10.0 g, 33.0 mmol) in ethylene glycol (20 mL) was stirred at 180° C. for 2 h. After cooling to RT, H2O (100 mL) was added and the mixture was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure; the residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1) to afford the title compound as a white solid (9.6 g, 100%). MS (ES+) C13H9F3N4OS requires: 326. found: 327 [M+H]+; 1H NMR (500 MHz, DMSO) 8.27 (s, 1H), 8.15 (d, J=8.5 Hz, 2H), 7.48 (d, J=8.0 Hz, 2H), 2.43 (s, 3H).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×100 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1)

Sources & evidence

ORD record
ord-2fb116785f0e4dac8ce870e9740867e6
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

Loading…