Hydrazine hydrate (1:1) → HCID 86711938, compound

HRID 1475247Notes

Reaction equation

HRID 1475247 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15](OCC)=[O:16])[S:13][CH:14]=2)=[CH:6][CH:5]=1.O.[NH2:23][NH2:24]>CO>[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]([NH:23][NH2:24])=[O:16])[S:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 61385373HCID 61385373, compound

Product 1

HCID 86711938HCID 86711938, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(4-(trifluoromethoxy)phenyl)thiazole-2-carboxylate (10.0 g, 31.5 mmol) in MeOH (80 mL) was added hydrazine hydrate (1.95 g, 33.1 mmol; 85%) dropwise over 15 minutes, and the resulting mixture was stirred for a further 16 h at RT. The mixture was then concentrated under reduced pressure to half volume, and H2O (30 mL) was added. A white solid precipitated, was filtered, washed with H2O (3×30 mL) and dried to afford the title compound as a white solid (9.6 g, 100%). MS (ES+) C11H8F3N3O2S requires: 303. found: 304[M+H]+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure to half volume, and H2O (30 mL)
  2. additionwas added
  3. customA white solid precipitated
  4. filtrationwas filtered
  5. washwashed with H2O (3×30 mL)
  6. customdried

Sources & evidence

ORD record
ord-f56a7b38f96c4df0b9c8cd5d00f04c5d
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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