Sodium hydride → HCID 67572455, compound

HRID 1736735Notes

Reaction equation

[C:1]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[C:30]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:25][CH:24]=1>CN(C)C=O.C(OCC)(=O)C>[N+:16]([C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:25][CH:24]=1)[C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])([O-:18])=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

2.5 g (0.01 mol) of 2-pentanoylamino-5-methoxy-nitrobenzene are dissolved in 30 ml of dimethylformamide, treated with 550 mg (0.11 mol) of sodium hydride (50% in oil) and stirred for 30 minutes at 80° C. 3.5 g (0.01 mol) of tert.butyl 4'-bromomethyl-biphenyl-2-carboxylate are then added and stirred for a further 2 hours at 80° C. The solvent is distilled off in vacuum, the oily residue obtained is dissolved in ethyl acetate, washed with water and evaporated in vacuum after drying over sodium sulphate. A yellowish oil is obtained after column chromatography (silica gel: 0.06-0.2 mm, eluting agent: methylene chloride).

Workup

stirringstirred for a further 2 hours at 80° C
distillationThe solvent is distilled off in vacuum
customthe oily residue obtained
washwashed with water
customevaporated in vacuum
dry with materialafter drying over sodium sulphate
customA yellowish oil is obtained
washafter column chromatography (silica gel: 0.06-0.2 mm, eluting agent: methylene chloride)

Sources & evidence

ORD record: ord-74aa4ea9fd7f4b95b97d12356a7b18c1
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541229

Reaction notes

Loading…