Potassium Carbonate → tert-Butyl (2-((5-methoxy-2-nitrophenyl)amino)ethyl)carbamate

HRID 501462Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11](F)[CH:10]=1.[C:19]([NH:26][CH2:27][CH2:28][NH2:29])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CS(C)=O>[C:22]([O:21][C:19](=[O:20])[NH:26][CH2:27][CH2:28][NH:29][C:11]1[CH:10]=[C:9]([O:8][CH3:7])[CH:14]=[CH:13][C:12]=1[N+:15]([O-:17])=[O:16])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

A 2 L flask equipped with a stir bar was charged with DMSO (800 mL), K2CO3 (161 g, 1.6 mol) and 4-methoxy-2-fluoro-1-nitrobenzene (100 g, 0.58 mol). Mono-N-Boc-1,2-diaminoethane (94 g, 0.55 mol) was added to the reaction mixture and stirred for 12 h at 60° C. The reaction mixture was triturated with ice cold water (1.2 L) and the resulting yellow precipitate was collected by vacuum filtration. The precipitate was washed several times with water (5×1 L) and dried on a high vacuum for 48 h to give the desired product as a bright yellow solid (178 g, 98%.)

Workup

customA 2 L flask equipped with a stir bar
customThe reaction mixture was triturated with ice cold water (1.2 L)
filtrationthe resulting yellow precipitate was collected by vacuum filtration
washThe precipitate was washed several times with water (5×1 L)
customdried on a high vacuum for 48 h

Sources & evidence

ORD record: ord-3a97c217a53a4e92aaeaf0a4fdada9cb
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772266B2

Reaction notes

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