HCID 68485467, compound → HCID 54612798, compound

HRID 1966057Notes

Reaction equation

HRID 1966057 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[S:13][CH2:14][C:15]#[N:16]>CCO.Cl>[NH2:16][C:15]1[CH2:14][S:13][C:3]2[CH:4]=[C:5]([O:8][C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

3

Reactant 1

HCID 68485467HCID 68485467, compound

Product 1

HCID 54612798HCID 54612798, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

A solution of 2-[2-amino-5-(trifluoromethoxy)phenylthio]-acetonitrile (0.70 g, 2.82 mmol) in 5% EtOH/HCl (20 ml) is refluxed for 2 hours. The solvent is then evaporated under vacuum and the residue diluted with H2O. The resulting aqueous solution is washed with CHCl3, basified with conc. NH4OH and the precipitate extracted with CHCl3. The combined organic extracts are dried over Na2SO4 and concentrated to give the product as a pale yellow solid (0.45 g, 64% yield, m.p. 94-96° C.). 1H-NMR (CDCl3): 3.14 (s, 2H), 5.04 (br s, 2H), 6.92-7.10 (m, 3H). MS (ESI): m/z 249 (M+H+).

Workup

  1. customThe solvent is then evaporated under vacuum
  2. additionthe residue diluted with H2O
  3. washThe resulting aqueous solution is washed with CHCl3
  4. extractionthe precipitate extracted with CHCl3
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bd5f08ab798144eeafdad4ec4a7b51c4
Source dataset
uspto-grants-2013_04
Patent number
US08420634B2

Reaction notes

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