Sec-Butylamine → Butralin

HRID 2294660Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](OC)=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:19]([NH2:23])([CH2:21][CH3:22])[CH3:20]>>[CH:19]([NH:23][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[N+:16]([O-:18])=[O:17])([CH2:21][CH3:22])[CH3:20]

Participants

Reactant 2

HCID 24874Sec-Butylamine

HCID 42526024-tert-Butyl-2,6-dinitroanisole

Product 1

HCID 36565Butralin

Procedure

An alternative synthesis for N-sec-butyl-4-tert-butyl-2,6-dinitroaniline is set forth in U.S. Pat. Nos. 4,289,907 and 4,395,572 to Chan. The starting material in this synthesis is a nitrophenol such as 2,6-dinitro-4-tert-butylphenol. The nitrophenol is methylated by reaction with methyl iodide/potassium carbonate to produce 4-tert-butyl-2,6-dinitroanisole. The 4-tert-butyl-2,6-dinitroanisole is then reacted with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline. While effective in producing the desired product, this process also suffers from a number of distinct disadvantages.

Sources & evidence

ORD record: ord-f00439e5e9c34729baa88db805f8a657
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05689006

Reaction notes

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