Phosgene → 1-[1-(3-Methyl-butyl)-5-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-1H-benzoimidazol-2-ylmethyl]-1,3-dihydro-benzoimidazol-2-one

HRID 896316Notes

Reaction equation

HRID 896316 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]2[N:9]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:10]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:22])=[N:11][C:7]=2[CH:6]=1)=[NH:4].[C:30](Cl)(Cl)=[O:31]>>[CH3:27][CH:25]([CH3:26])[CH2:24][CH2:23][N:9]1[C:8]2[CH:28]=[CH:29][C:5]([C:3]3[NH:4][C:30](=[O:31])[O:1][N:2]=3)=[CH:6][C:7]=2[N:11]=[C:10]1[CH2:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]1=[O:22]

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 178446109HCID 178446109, compound

Product 1

HCID 1356868751-[1-(3-Methyl-butyl)-5-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-1H-benzoimidazol-2-ylmethyl]-1,3-dihydro-benzoimidazol-2-oneYield 26.3%

Procedure

N-Hydroxy-1-(3-methyl-butyl)-2-(2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1H-benzoimidazole-5-carboxamidine (75 mg, 0.191 mmol) was treated with phosgene (1 ml, 1.91 mmol, 1.92 M in toluene) and heated to reflux for 2.5 h. The mixture was cooled and stirred for 48 h. A white precipitate was isolated by filtration to give 21 mg (26%) of 1-[1-(3-Methyl-butyl)-5-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-1H-benzoimidazol-2-ylmethyl]-1,3-dihydro-benzoimidazol-2-one.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 h
  3. temperatureThe mixture was cooled
  4. customA white precipitate was isolated by filtration

Sources & evidence

ORD record
ord-0ded835ccc2040cd804565e676837fc9
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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