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

HRID 2353278Notes

Reaction equation

HRID 2353278 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=80 (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-5ea3f27194e644f6b8b3c6ec6302217d
Source dataset
uspto-grants-2010_07
Patent number
US07750010B2

Reaction notes

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