O,O-Dipyridin-2-yl carbonothioate → 1,4-Dimethyl-5-benzimidazolylisothiocyanate

HRID 2260735Notes

Reaction equation

HRID 2260735 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[NH2:17][C:18]1[CH:27]=[CH:26][C:21]2[N:22]([CH3:25])[CH:23]=[N:24][C:20]=2[C:19]=1[CH3:28]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:25][N:22]1[C:21]2[CH:26]=[CH:27][C:18]([N:17]=[C:8]=[S:9])=[C:19]([CH3:28])[C:20]=2[N:24]=[CH:23]1

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 224622221,4-Dimethyl-1H-benzo[d]imidazol-5-amine

Product 1

HCID 153408751,4-Dimethyl-5-benzimidazolylisothiocyanate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-2-pyridyl thionocarbonate (494 mg) and 4-dimethylaminopyridine (0.01 g) in methylene chloride (40 mL) is added dropwise over 30 minutes, a solution of 5-amino-1,4-dimethylbenzimidazole (176 mg) in methylene chloride (20 mL). The mixture is stirred for 3 hours at room temperature, then rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 50% ethyl acetate/hexane, to afford 1,4-dimethyl-5-benzimidazolylisothiocyanate as a white solid.

Workup

  1. customThe residue is purified by flash chromatography on silica gel
  2. washeluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e02485b876dd470382ee710ed911650d
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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