O,O-Dipyridin-2-yl carbonothioate → HCID 18400157, compound

HRID 1019087Notes

Reaction equation

HRID 1019087 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7]([CH3:9])=[N:8][C:4]=2[C:3]=1[CH3:19].C1C=C(O[C:27](OC2N=CC=CC=2)=[S:28])N=CC=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:13]([O:12][C:10]([N:6]1[C:5]2[CH:17]=[CH:18][C:2]([N:1]=[C:27]=[S:28])=[C:3]([CH3:19])[C:4]=2[N:8]=[C:7]1[CH3:9])=[O:11])([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 18400143HCID 18400143, compound

Product 1

HCID 18400157HCID 18400157, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-amino-1-t-butoxycarbonyl-2,4-dimethylbenzimidazole (1.1 g, 4.2 mmol) in methylene chloride (60 mL) is added dropwise over 30 minutes to a solution of di-2-pyridyl thionocarbonate (1.9 g, 8.2 mmol) and 4-dimethylaminopyridine (0.1 g) in methylene chloride (150 mL). The mixture is stirred for 2 hours 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-t-butoxycarbonyl-2,4-dimethyl-5-isothiocyanatobenzimidazole 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-4b1100bc2547475886ca2cf6b6f65f7a
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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