Sec-Butylamine → Butralin

HRID 1377013Notes

Reaction equation

HRID 1377013 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1OC)([O-:3])=[O:2].[CH:19]([NH2:23])([CH2:21][CH3:22])[CH3:20]>>[CH:19]([NH:23][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH2:21][CH3:22])[CH3:20]

Participants

3

Reactant 2

HCID 24874Sec-ButylamineHCID 42526024-tert-Butyl-2,6-dinitroanisole

Product 1

HCID 36565Butralin

Procedure

More specifically, the process for producing N-sec-butyl-4-tert-butyl-2,6-dinitroaniline comprises reacting 4-tert-butylphenol with dimethyl sulfate to produce 4-tert-butylanisole. The 4-tert-butylanisole is then reacted with nitrating agent to produce 2,6-dinitro-4-tert-butylanisole. The 2,6-dinitro-4-tert-butylanisole is then reacted with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline.

Sources & evidence

ORD record
ord-d2ede07befc14f82aecf2bda3a9978f5
Source dataset
uspto-grants-1997_09
Patent number
US05663441

Reaction notes

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