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

HRID 2295041Notes

Reaction equation

HRID 2295041 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.ClCl>[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

6

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 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

To a solution of di-2-pyridyl thionocarbonate (DPT) (14.3 g) and 4-dimethylaminopyridine (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 CH2 Cl2 (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-2c27c95c552f4332a0e0b3fa680c1e1f
Source dataset
uspto-grants-1997_11
Patent number
US05691370

Reaction notes

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