Indole → HCID 12452825, compound

HRID 1500847Notes

Reaction equation

HRID 1500847 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[S-:10][C:11]#[N:12].[NH4+].OOS([O-])=O.[K+]>CO>[N:12]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[C:11]=[S:10]

Participants

5

Reactant 3

HCID 798IndoleHCID 15666Ammonium thiocyanateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 12452825HCID 12452825, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of indole (2.0 g, 17.1 mmol) and ammonium thiocyanate (1.95 g, 25.6 mmol) in methanol (150 mL) was treated with oxone (15.7 g, 25.6 mmol) and allowed to stir at RT for overnight till TLC showed all starting material consumed. The reaction solution was evaporated in vacuum. The residue was purified by chromatography on silica gel (EtOAc:PE=5/95) to afford 2.2 g of 3-isothiocyanato-1H-indole as yellow solid (yield: 73%). MS obsd. (ESI+) [(M+H)+] 175.1, 1H NMR: (400 MHz, CDCl3) δ ppm: 8.67 (brs, 1H), 7.82-7.80 (m, 1H), 7.52 (d, J=3.0 Hz, 1H), 7.44-7.43 (m, 1H), 7.34-7.30 (m, 2H).

Workup

  1. customconsumed
  2. customThe reaction solution was evaporated in vacuum
  3. customThe residue was purified by chromatography on silica gel (EtOAc:PE=5/95)

Sources & evidence

ORD record
ord-2877ad3819654ae88789a9df1fce7485
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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