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

HRID 1042678Notes

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-nitrophenyl)acetamide (80 g, 253, mmol) and potassium carbonate (70 g, 506 mmol) were combined in THF (1.75 L), and the mixture was cooled to 0° C. N,N-Dimethylamine (40 ml of a 2 M solution in THF, 800 mmol) was then added to the mixture through an addition funnel over a 30-minute period. The mixture was then stirred at room temperature for 16 hours. The mixture was then filtered and the filtrate was concentrated. The crude material was purified by silica chromatography using 50% EtOAc:hexanes as the eluent to give N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide as a brown solid.

Workup

filtrationThe mixture was then filtered
concentrationthe filtrate was concentrated
customThe crude material was purified by silica chromatography

Sources & evidence

ORD record: ord-8677bbade54841629889493ab3089d48
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557996B2

Reaction notes

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