Water → 1-Benzyl-4-benzyloxy-1,3-dihydro-benzoimidazol-2-one

HRID 730561Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[C:10]([NH2:23])=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl.O>ClCCl>[CH2:1]([N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[NH:23][C:32]1=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N*1*-Benzyl-3-benzyloxy-benzene-1,2-diamine (4.60 g, 15.11 mmol) in 100 mL dichloromethane at 0° C. was added triethylamine (4.201 mL, 30.22 mmol) followed by portionwise addition of triphosgene (1.57 g, 5.29 mmol). The resulting solution was stirred for 2 hours at 0° C. The reaction mixture was allowed to warm to room temperature and was then added to 200 mL water. The organic phase was separated, washed with 100 mL 10% aqueous HCl, 100 mL saturated aqueous sodium bicarbonate, and 100 mL brine, dried over sodium sulfate, and concentrated in vacuo to give 4.60 g (13.92 mmol, 92%) of 1-benzyl-4-benzyloxy-1,3-dihydro-benzoimidazol-2-one as a tan solid. MS: 331 (M+H)+.

Workup

temperatureto warm to room temperature
customThe organic phase was separated
washwashed with 100 mL 10% aqueous HCl, 100 mL saturated aqueous sodium bicarbonate, and 100 mL brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b11db3e8c0dd418786adb6b3283269d2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582760B2

Reaction notes

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