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

HRID 1042715Notes

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 filtered and the filtrate concentrated. The crude material was purified by silica chromatography eluting with 50% EtOAc:hexanes to give N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide as a brown solid.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate concentrated
customThe crude material was purified by silica chromatography
washeluting with 50% EtOAc

Sources & evidence

ORD record: ord-1c78fceecee94151a772334bce875cf8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557996B2

Reaction notes

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