Dimethylformamide → HCID 178488015, compound

HRID 1500386Notes

Reaction equation

HRID 1500386 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:8](=S)[NH2:9])(C)C.O.[NH2:19]N.C[N:22]([CH:24]=O)C>C(O)=O>[CH3:1][O:4][C:5]1[CH:6]=[C:7]([C:8]2[N:22]=[CH:24][NH:19][N:9]=2)[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 86730375HCID 86730375, compound

Product 1

HCID 178488015HCID 178488015, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
10 °C

Procedure

3-Isopropoxy-5-(trifluoromethyl)benzothioamide (646 g; 2.74 moles) was combined with hydrazine hydrate (140 g; 4.4 moles) and DMF (3200 mL; 5V). The mixture was stirred for 30 minutes and cooled to 10° C. To this reaction mixture was added formic acid (3200 mL) dropwise. Reaction mixture was heated to 90 to 100° C. and maintained for 12 hrs. After reaction completion by HPLC, reaction mass was cooled to 25 to 30° C. and quenched with ice-cold water. The mixture was extracted in MTBE. The organic layer was washed with brine followed by aqueous sodium bicarbonate, and concentrated under vacuum. The residue was chased off using hexane, the resulting residue was slurried at 10° C. for 1 hour. The solid obtained was filtered and dried for 12 hours at 25 to 30° C. to yield 550 g (2.26 moles: 82%) of the product 3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole. HPLC purity—95.24% a/a.

Workup

  1. customReaction mixture
  2. temperaturewas heated to 90 to 100° C.
  3. temperaturemaintained for 12 hrs
  4. customAfter reaction completion
  5. customby HPLC, reaction mass
  6. temperaturewas cooled to 25 to 30° C.
  7. customquenched with ice-cold water
  8. extractionThe mixture was extracted in MTBE
  9. washThe organic layer was washed with brine
  10. concentrationconcentrated under vacuum
  11. waitthe resulting residue was slurried at 10° C. for 1 hour
  12. customThe solid obtained
  13. filtrationwas filtered
  14. customdried for 12 hours at 25 to 30° C.

Sources & evidence

ORD record
ord-21498117994e472aa9bc229c91abb9f9
Source dataset
uspto-grants-2015_12
Patent number
US09206158B2

Reaction notes

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