Thiophosgene → 2-Aminobenzimidazole

HRID 16542

Reaction equation

HRID 16542 reaction equation
[N-:1]=[C:2]=S.C(Cl)(Cl)=S.NC(N)=S.[CH:12]1([N:18]=[C:19]=[N:20]C2CCCCC2)C[CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])(O)=O.[Na+]>ClCCl.C1COCC1>[NH2:20][C:19]1[NH:18][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[N:1]=1

Participants

8

Reactant 5

HCID 10040ThiophosgeneHCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 178418790HCID 178418790, compound

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of an isothiocyanate (prepared by reacting the corresponding amine with thiophosgene) and a suitably substituted phenylenediamine in dry dichloromethane was stirred at rt overnight and evaporated to dryness. The resulting thiourea was then purified by e.g. column chromatography or reacted further as crude material. Thus, the thiourea was dissolved in THF, added a coupling reagent such as dicyclohexylcarbodiimide (DCC), and stirred at reflux temperature overnight. Aqueous NaHCO3 was added and the solution extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude 2-aminobenzimidazole which was subsequently purified by column chromatography or preparative LCMS.

Workup

  1. customprepared
  2. customevaporated to dryness
  3. customThe resulting thiourea was then purified by e.g. column chromatography
  4. customreacted further as crude material
  5. stirringstirred
  6. temperatureat reflux temperature overnight
  7. extractionthe solution extracted with EtOAc
  8. dry with materialThe combined organic phases were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ea4fa99f54042f2a8bc14db1550381c
Source dataset
uspto-grants-2010_06
Patent number
US07737167B2

Linked notes

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