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

HRID 18480

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 (10 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 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 washed several times with water (5×1 L)
customdried on a high vacuum for 48 h

Sources & evidence

ORD record: ord-da35237a06ea4009a1592d9924c75584
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741355B2

Linked notes

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