Dimethylamine → N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

HRID 491625Notes

Reaction equation

Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH3:25][NH:26][CH3:27]>C1COCC1>[C:15]([C:7]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:26]([CH3:27])[CH3:25])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Bromo-N-(2-tert-butyl-5-nitro-phenyl)-acetamide (Step B, 80 g, 253 mmol) and K2CO3 (70 g, 506 mmol) were combined in a 3 L 3-neck round bottom flask fitted with a mechanical stirrer, N2(g) inlet, and pressure equalizing addition funnel. THF (1.75 L) was added and the mixture cooled to 0° C. under N2(g). N,N-Dimethylamine (400 mL of a 2 M solution in THF, 800 mmol) was added to the mixture through the pressure equalizing addition funnel over 30 min. The mixture was gradually warmed to RT with stirring overnight. The reaction was quenched by filtering under vacuum and concentrating the filtrate under reduced pressure. The recovered material was eluted through a 36×7 cm column of silica gel with 50% EtOAc:Hexanes giving a brown solid.

Workup

customfitted with a mechanical stirrer, N2(g) inlet
additionaddition funnel
additionaddition funnel over 30 min
temperatureThe mixture was gradually warmed to RT
customThe reaction was quenched
filtrationby filtering under vacuum
concentrationconcentrating the filtrate under reduced pressure
washThe recovered material was eluted through a 36×7 cm column of silica gel with 50% EtOAc

Sources & evidence

ORD record: ord-338acbf132884d52a85c9a8c8ad80720
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531553B2

Reaction notes

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