O,O-Dipyridin-2-yl carbonothioate → HCID 22461231, compound

HRID 1275660Notes

Reaction equation

HRID 1275660 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6]([C:12]#[N:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C1C=C(O[C:21](OC2N=CC=CC=2)=[S:22])N=CC=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:12]([C:6]1[C:5]2[C:9](=[C:10]([CH3:11])[C:2]([N:1]=[C:21]=[S:22])=[CH:3][CH:4]=2)[NH:8][CH:7]=1)#[N:13]

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 22461235HCID 22461235, compound

Product 1

HCID 22461231HCID 22461231, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-amino-3-cyano-7-methylindole (0.155 g, 0.905 mmol) in methylene chloride (10 mL) is added di-2-pyridyl thionocarbonate (0.210 g, 0.905 mmol) followed by 4-dimethylaminopyridine (0.010 g, 0.0905 mmol). The resulting solution is stirred at room temperature for one hour followed by removal of the methylene chloride by rotary evaporation. The crude material is purified via silica gel column chromatography using 20% ethyl acetate/hexane as the eluting solvent. The product containing fractions are combined and the solvents removed by rotary evaporation to yield 0.154 g of 3-cyano-6-isothiocyanato-7-methylindole as a yellow solid (80% 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-34ee52caa4d44372b35ca9e43d09bde1
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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