Triphosgene → 1-[(4-Methylphenyl)sulfonyl]-4-nitro-1,3-dihydro-2H-benzimidazol-2-one

HRID 2426177Notes

Reaction equation

HRID 2426177 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>CC#N>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([N:11]2[C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=3[NH:1][C:23]2=[O:25])(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 141475022-amino-3-nitro-N-tosylaniline

Product 1

HCID 576637451-[(4-Methylphenyl)sulfonyl]-4-nitro-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(2-amino-3-nitrophenyl)-4-methylbenzenesulfonamide from Step A (2.00 g, 6.51 mmol) in CH3CN (100 mL) was added triphosgene (966 mg, 3.25 mmol) and the mixture was stirred at ambient temperature for 30 min. The precipitate was isolated by filtration and dried in vacuo to give the title compound. MS: m/z=334 (M+1).

Workup

  1. customThe precipitate was isolated by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-ec9a508821a643dd84d005bc73ee1d36
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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