O,O-Dipyridin-2-yl carbonothioate → HCID 12051208, compound

HRID 1019077Notes

Reaction equation

HRID 1019077 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[NH2:17][C:18]1[CH:26]=[C:25]([CH3:27])[C:21]2[N:22]=[CH:23][NH:24][C:20]=2[C:19]=1[CH2:28][CH3:29]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CO>[CH2:28]([C:19]1[C:20]2[NH:24][CH:23]=[N:22][C:21]=2[C:25]([CH3:27])=[CH:26][C:18]=1[N:17]=[C:8]=[S:9])[CH3:29]

Participants

6

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 12051207HCID 12051207, compound

Product 1

HCID 12051208HCID 12051208, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of di-2-pyridyl thionocarbonate (0.72 g, 3.11 mmol) and 4-dimethylaminopyridine (0.02 g) in ethyl acetate (50 mL) is added dropwise a solution of 5-amino-4-ethyl-7-methylbenzimidazole (0.42 g, 2.39 mmol) in ethyl acetate (20 mL) and methanol (5 mL). The mixture is stirred at room temperature for 3 hours, then rotary evaporated. The residue is purified by filtration on a short pad of silica gel, eluting with ethyl acetate, to afford 4-ethyl-5-isothiocyanato-7-methylbenzimidazole as a tan solid.

Workup

  1. filtrationThe residue is purified by filtration on a short pad of silica gel
  2. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-80da76ccdea74eec826c3468c01f62c0
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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