O,O-Dipyridin-2-yl carbonothioate → HCID 22461242, compound

HRID 1275665Notes

Reaction equation

HRID 1275665 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[CH2:20][C:21](=[O:27])[NH:22]2>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:17]([C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH2:20][C:21](=[O:27])[NH:22]2)=[C:8]=[S:9]

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 122374724-Aminoindolin-2-one

Product 1

HCID 22461242HCID 22461242, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (0.086 g, 0.706 mmol) and di-2-pyridyl thionocarbonate (0.983 g, 4.23 mmol) are added to a solution of 4-aminooxindole (0.523 g, 3.53 mmol) in methylene chloride. The resulting mixture is stirred at room temperature for two hours during which time a soluble solution forms. The methylene chloride is removed by rotary evaporation and the crude residue is purified via silica gel column chromatography using 40% ethyl acetate/hexanes as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.531 g of 4-isothiocyanatooxindole as a dark orange solid (79%, impure).

Workup

  1. customThe methylene chloride is 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-7cd395dfa04748e3b3887e2b2ff4fc26
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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