Potassium thiocyanate → HCID 58496319, compound

HRID 2039656Notes

Reaction equation

HRID 2039656 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[S-:16][C:17]#[N:18].[K+]>CS(O)(=O)=O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:17](=[S:16])[NH2:18])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 119941974-Methoxydibenzofuran

Product 1

HCID 58496319HCID 58496319, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

To a mixture of 4-methoxydibenzo[b,d]furan (1 g, 5.05 mmol) in methane sulphonic acid (11 mL), potassium thiocyanate (1 g, 10.29 mmol) was added at 0-5° C. Subsequently the reaction mass was stirred at room temperature for 3 h. The reaction mixture was poured into crushed ice and filtered. The solid was washed with hexane and dried, to furnish the required product in 70% yield; Rf 0.25 (Ethyl acetate:Hexane (3:7); HPLC (purity); 1H-NMR (CDCl3) δ: 4.08 (s, 3H), 6.97 (d, 1H), 7.26-7.30 (m, 1H), 7.33-7.37 (m, 1H), 7.65 (d, 1H), 7.69 (d, 1H), 7.94 (d, 1H), 8.31 (d, 1H); 91.4%; MS m/z: 258.1 (M+1).

Workup

  1. additionwas added at 0-5° C
  2. additionThe reaction mixture was poured
  3. custominto crushed ice
  4. filtrationfiltered
  5. washThe solid was washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-4701fda146994620b35e93aa23da82da
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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