Ammonium thiocyanate → HCID 22574114, compound

HRID 23410

Reaction equation

HRID 23410 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[S-:12][C:13]#[N:14].[NH4+]>CO.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([S:12][C:13]#[N:14])=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 15666Ammonium thiocyanateHCID 766596-Methoxy-1H-indole

Product 1

HCID 22574114HCID 22574114, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Using the procedure described in Tetrahedron Letters 40 (1999), 1195-1196, 6-methoxy-1H-indole (1.0 g, 6.8 mmole) and ammonium thiocyanate (0.621 g, 8.1 mmole) were dissolved in methanol (35 ml) and treated with ceric ammonium nitrate (8.56 g, 15.6 mmole)in methanol (175 ml) at room temperature. The reaction mixture was stirred for 15 m and then diluted with water (700 ml) and extracted with methylene chloride (4×125 ml). The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by column chromatography (silica gel) using ethyl acetate:hexane (1:9) as the eluting solvent to afford 6-methoxy-3-thiocyanato-1H-indole (0.40 g 29% yield).

Workup

  1. extractionextracted with methylene chloride (4×125 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-debb577357664b9e99297c30e47c2861
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Linked notes

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