4-Chloro-3,5-dinitrobenzotrifluoride → Benfluralin

HRID 1112187Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH2:18]([NH:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21]>>[CH2:18]([N:22]([CH2:23][CH3:24])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16])[CH2:19][CH2:20][CH3:21]

Participants

Reactant 2

HCID 98094-Chloro-3,5-dinitrobenzotrifluoride

HCID 25914Butylethylamine

Product 1

HCID 2319Benfluralin

Procedure

Various portions of the 1-chloro-2,6-dinitro-4-(trifluoromethyl)benzene (treated as described above) were aminated with N-n-butyl-N-ethylamine, to produce N-n-butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline, or with N-ethyl-N-methallylamine, to produce N-ethyl-N-methallyl-2,6-dinitro-4-(trifluoromethyl)aniline. Each product was analyzed for nitrosamine content. The N-n-butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline was found to contain 7 or 20 ppm of N-nitroso-N-n-butyl-N-ethylamine (two different analytical laboratories) and the N-ethyl-N-methallyl-2,6-dinitro-4-(trifluoromethyl)aniline was found to contain 16 ppm of N-nitroso-N-ethyl-N-methallylamine.

Sources & evidence

ORD record: ord-460d2e45586e46db920ce3d051ddd1b2
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04120905

Reaction notes

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