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

HRID 551024Notes

Reaction equation

HRID 551024 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-efbc20d747324ee2b73a53ba376e09f8
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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