Hydrochloric Acid → HCID 59707057, compound

HRID 221961Notes

Reaction equation

[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]2=[O:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>O.CN(C=O)C>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([CH2:29][C:28]3[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=3)[C:11]2=[O:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of compound N (1.12 g, 4.0 mmol) in abs. DMF (30 mL) there were added 4-nitrobenzyl bromide (864 mg, 4.0 mmol), potassium carbonate (1.14 g, 8.30 mmol), and a catalytic amount of potassium iodide under a blanket of argon. The reaction mixture was heated to 75° C. over a period of 4 h. Following cooling, the reaction mixture was poured into a mixture of ice (300 g) and 2N hydrochloric acid solution in H2O (200 mL), and the reaction mixture was stirred for 1 hour. The resulting solid matter was separated through a frit and dried in vacuo over calcium chloride. The desired product 1-(4-tert-butylbenzyl)-3-(4-nitrobenzyl)-1,3-dihydrobenzimidazol-2-one (P) was obtained in an adequately pure form for synthetic purposes in a yield of 1.48 g (89% of theory).

Workup

temperatureFollowing cooling
customThe resulting solid matter was separated through a frit
dry with materialdried in vacuo over calcium chloride

Sources & evidence

ORD record: ord-85d9282dddd041b0a6ca6b0b69639fce
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207182B2

Reaction notes

Loading…