O,O-Dipyridin-2-yl carbonothioate → HCID 12049865, compound

HRID 1275674Notes

Reaction equation

HRID 1275674 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[NH2:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20]([Cl:27])=[CH:21][NH:22]2>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:27][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[CH:26][C:18]=2[N:17]=[C:8]=[S:9])[NH:22][CH:21]=1

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 12049864HCID 12049864, compound

Product 1

HCID 12049865HCID 12049865, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (0.031 g, 0.256 mmol) and di-2-pyridyl thionocarbonate (0.983 g, 4.23 mmol) are added to a solution of 4-amino-3-chloroindole (0.655 g, 2.82 mmol) in methylene chloride. The resulting mixture is stirred at room temperature for 1 hour. The volatile organics are removed by rotary evaporation and the crude residue is purified via silica gel column chromatography using 20% ethyl acetate/hexanes as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.511 g of 3-chloro-4-isothiocyanatoindole as a yellow solid (96%).

Workup

  1. customThe volatile organics are removed by rotary evaporation
  2. customthe crude residue is purified via silica gel column chromatography
  3. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-d478cbb1f30e4ee8845ca305ae261f85
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

Loading…