O,O-Dipyridin-2-yl carbonothioate → 1h-Benzimidazole-1-carboxylic acid,5-isothiocyanato-4-methyl-,1,1-dimethylethyl ester

HRID 2260724Notes

Reaction equation

HRID 2260724 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[NH2:17][C:18]1[CH:33]=[CH:32][C:21]2[N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:23]=[N:24][C:20]=2[C:19]=1[CH3:34]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:28]([O:27][C:25]([N:22]1[C:21]2[CH:32]=[CH:33][C:18]([N:17]=[C:8]=[S:9])=[C:19]([CH3:34])[C:20]=2[N:24]=[CH:23]1)=[O:26])([CH3:29])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 15896318HCID 15896318, compound

Product 1

HCID 214727251h-Benzimidazole-1-carboxylic acid,5-isothiocyanato-4-methyl-,1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-2-pyridyl thionocarbonate (DPT) (14.3 g) and 4dimethylaminopyridine (0.1 g) in CH2Cl2 (500 mL) is added dropwise over 30 minutes a solution of 5-amino-1-tert-butoxycarbonyl-4-methylbenzimidazole (7.82 g) in CH2Cl2 (250 mL). The mixture is stirred for 15 minutes at room temperature then rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 10% ethyl acetate/hexane to afford 1-tert-butoxycarbonyl-4-methyl-5-benzimidazolylisothiocyanate as a white solid.

Workup

  1. customThe residue is purified by flash chromatography on silica gel
  2. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a639cd0fb3244291aa240228ad7b12ab
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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