O,O-Dipyridin-2-yl carbonothioate → 6-Isothiocyanato-7-methylindole

HRID 1275657Notes

Reaction equation

HRID 1275657 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C1C=C(O[C:19](OC2N=CC=CC=2)=[S:20])N=CC=1>C(Cl)Cl>[N:1]([C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1)=[C:19]=[S:20]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 158963787-methyl-1H-indol-6-amine

Product 1

HCID 158963796-Isothiocyanato-7-methylindoleYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-amino-7-methylindole (1.0 g, 6.84 mmol) in methylene chloride (50 mL) is added di-2-pyridyl thionocarbonate (1.59 g, 6.84 mmol). The resulting solution is stirred at room temperature for two hours followed by removal of the methylene chloride by rotary evaporation. The crude material is purified via silica gel column chromatography using 10% ethyl acetate/hexane as the eluting solvent. The product containing fractions are combined and the solvents removed by rotary evaporation to yield 0.90 g of 6-isothiocyanato-7-methylindole as a white solid (70% yield).

Workup

  1. customfollowed by removal of the methylene chloride by rotary evaporation
  2. customThe crude material is purified via silica gel column chromatography
  3. additionThe product containing fractions
  4. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-d60a1724c27447bea73ce600b591400c
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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