Ethyl Acetate → benzyl N-[[(1,4-dimethylbenzimidazol-5-yl)amino]-(phenylmethoxycarbonylamino)methylidene]carbamate

HRID 1976112Notes

Reaction equation

HRID 1976112 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH3:9])[CH:7]=[N:8][C:4]=2[C:3]=1[CH3:12].C([N:15]=[C:16](S)[N:17](C(OCC1C=CC=CC=1)=O)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])C.[C:39]([O:42][CH2:43][CH3:44])(=[O:41])C>CO>[CH2:43]([O:42][C:39]([N:15]=[C:16]([NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[NH:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH3:9])[CH:7]=[N:8][C:4]=2[C:3]=1[CH3:12])=[O:41])[C:44]1[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 224622221,4-Dimethyl-1H-benzo[d]imidazol-5-amineHCID 178465517HCID 178465517, compound

Product 1

HCID 178430656benzyl N-[[(1,4-dimethylbenzimidazol-5-yl)amino]-(phenylmethoxycarbonylamino)methylidene]carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 250 mg of 5-amino-1,4-dimethylbenzimidazole in 75 mL of ethyl acetate and 10 mL of methanol are added 789 mg of ethyl N,N-bis(benzyloxycarbonyl)pseudothiourea and 665 mg of mercuric acetate and the mixture is stirred at room temperature for 15 hours. The mixture is filtered on Celite and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 5% methanol/ethyl acetate to provide 590 mg of 5-[N2,N3-bis(benzyloxycarbonyl)guanidino]-1,4-dimethybenzimidazole as a white solid.

Workup

  1. filtrationThe mixture is filtered on Celite and rotary evaporated
  2. customThe residue is purified by flash column chromatography on silica gel
  3. washeluting with 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-77e8a7d6fff44285a26b08f67ee2d54b
Source dataset
uspto-grants-2001_05
Patent number
US06225331B1

Reaction notes

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