Triphosgene → 4-Nitro-1H-benzo[d]imidazol-2(3H)-one

HRID 641379Notes

Reaction equation

HRID 641379 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[N+:13]([C:16]1[C:17]([NH2:23])=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]>CC#N>[N+:13]([C:16]1[C:17]2[NH:23][C:5](=[O:11])[NH:22][C:18]=2[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 41498284-Nitro-1H-benzo[d]imidazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphosgene (56 g, 188.8 mol) was added portionwise over 15 min to a solution of 3-nitro-1,2-phenylenediamine (25.5 g, 167 mol) in CH3CN (400 mL) at 0° C. and the mixture was allowed to warm to ambient temperature after 30 min. The reaction was concentrated in vacuo, diluted with toluene (100 mL) and the solid precipitate was collected by filtration to give the title compound. MS: m/z=180 (M+1).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with toluene (100 mL)
  3. filtrationthe solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-9b996c82427e49d9bdd9e2ccf5ee0e85
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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