Potassium cyanate → HCID 135964795, compound

HRID 893527Notes

Reaction equation

HRID 893527 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]2[S:13][CH2:12][CH2:11][CH2:10][S:9]2)=[CH:6][C:5]([NH:14][N:15]=[CH:16][CH3:17])=[C:4]([F:18])[CH:3]=1.[O-:19][C:20]#[N:21].[K+].Cl[O-].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([CH:8]2[S:9][CH2:10][CH2:11][CH2:12][S:13]2)=[CH:6][C:5]([N:14]2[C:20](=[O:19])[NH:21][C:16]([CH3:17])=[N:15]2)=[C:4]([F:18])[CH:3]=1

Participants

7

Reactant 3

HCID 11378442Potassium cyanate2×HCID 23665760Sodium HypochloriteHCID 86745947HCID 86745947, compound2×

Product 1

HCID 135964795HCID 135964795, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

To a stirred mixture of 5.00 g (0.0145 mole) of acetaldehyde 4-chloro-2-fluoro-5-(1,3-dithian-2-yl)phenylhydrazone in 50 mL of acetic acid is added dropwise a solution of 1.38 g (0.017 mole) of potassium cyanate in 5 mL of water. This mixture is stirred at 15° C. for approximately 1.5 hour. Additional aqueous potassium cyanate solution may be added if analysis of the reaction mixture by thin layer chromatography indicates the presence of acetaldehyde 4-chloro-2-fluoro-5-(1,3-dithian-2-yl)phenylhydrazone. While maintaining a temperature of 15° C., 30 mL of an aqueous, 5% sodium hypochlorite solution is added. This mixture is stirred at 15° C. for approximately one hour. The solvents are removed by distillation under reduced pressure to leave a residue. This residue is dissolved in ethyl acetate and is washed in succession with an aqueous, saturated sodium bicarbonate solution, water, and an aqueous, saturated sodium chloride solution. The washed organic solution is dried over anhydrous magnesium sulfate and is filtered. The filtrate is evaporated under reduced pressure to yield 1-[4-chloro-2-fluoro-5-(1,3-dithian-2-yl)phenyl]-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one.

Workup

  1. additionis added
  2. stirringThis mixture is stirred at 15° C. for approximately one hour
  3. customThe solvents are removed by distillation under reduced pressure
  4. customto leave a residue
  5. washis washed in succession with an aqueous, saturated sodium bicarbonate solution, water
  6. dry with materialThe washed organic solution is dried over anhydrous magnesium sulfate
  7. filtrationis filtered
  8. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-b51afe984bae47639ab0bad02772efc1
Source dataset
uspto-grants-1992_06
Patent number
US05125958

Reaction notes

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