Water → 1-Benzyl-1H-benzo[d]imidazol-2(3H)-one

HRID 2229423Notes

Reaction equation

HRID 2229423 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.O>ClCCl>[CH:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]2[C:17](=[O:19])[NH:1][C:2]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 2735482N1-Benzylbenzene-1,2-diamine

Product 1

HCID 7365051-Benzyl-1H-benzo[d]imidazol-2(3H)-oneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[N-(2-Aminophenyl)]-benzylamine (15.1 mmol, 3.0 g) in dichloromethane (80 ml) is charged with triphosgene (5.3 mmol, 1.57 g) in dichloromethane (40 ml) and is stirred at room temperature over the weekend. The suspension is poured into water (100 g) and is extracted with dichloromethane (2×50 ml). The organic layer is a suspension The colorless solid is filtered off, is dried in vacuo and is recrystallized from ethyl acetate to give the title product (81%)(R1=H, R2=benzyl, n=0).

Workup

  1. extractionis extracted with dichloromethane (2×50 ml)
  2. filtrationis filtered off
  3. customis dried in vacuo
  4. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8ced66928dcb40ffa410b7fe06355873
Source dataset
uspto-grants-2002_07
Patent number
US06420410B1

Reaction notes

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