Sodium Cyanate → HCID 12043637, compound

HRID 1582701Notes

Reaction equation

HRID 1582701 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:19]=[CH:18][NH:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[O-:20][C:21]#[N:22].[Na+]>C(O)(=O)C.O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:19]=[CH:18][N:17]([C:21]([NH2:22])=[O:20])[N:16]=3)=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 517096Sodium CyanateHCID 178505902HCID 178505902, compound

Product 1

HCID 12043637HCID 12043637, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[4-(4-fluorophenylthio)phenyl]-1H-pyrazole (85 mg, 0.31 mmol) in 1.5 mL glacial acetic acid was treated with a solution of sodium cyanate (31 mg, 0.47 mmol) in 0.5 mL of water. The resulting white suspension was stirred at room temperature overnight. The suspension was then diluted with 10 mL of EtOAc, resulting in a yellow solution which was washed with water and sat. NaHCO3 solution, dried over Na2SO4 and evaporated. The residue was trituated with 3 mL of 25% EtOAc/hexane. The white solid that formed was collected by filtration and dried to give 65 mg (66%) of the title compound, mp 150-155° C. (TLC Rf=0.22 (25% EtOAc/hexane)). 1H NMR (300 MHz, CDCl3): δ 8.27 (d, J=2.1 Hz, 1H, pyrazole H), 7.77 (d, J=7.5 Hz, 2H, PhH), 7.48-7.06 (m, 6H, PhH), 6.71 (d, J=2.1 Hz, 1H, pyrazole H), 5.31 (br s, 2H, NH2).

Workup

  1. customresulting in a yellow solution which
  2. washwas washed with water and sat. NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe white solid that formed
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-089e3697b6f74b3492d0a250829c2c83
Source dataset
uspto-grants-2004_05
Patent number
US06737418B2

Reaction notes

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