Toluene → Butralin

HRID 1678833Notes

Reaction equation

HRID 1678833 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]=1Cl)([O-:3])=[O:2].[CH:18]([NH2:22])([CH2:20][CH3:21])[CH3:19].C1(C)C=CC=CC=1>C(O)C>[CH:18]([NH:22][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])([CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24874Sec-ButylamineHCID 751764-tert-Butyl-2,6-dinitrochlorobenzene2×

Product 1

HCID 36565Butralin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

One gram of 2,6-dinitro-4-t-butylchlorobenzene was allowed to react with one gram of sec-butylamine by adding the amine dropwise to a refluxing mixture of 50 ml. dry toluene, and the 2,6-dinitro-4-t-butylchlorobenzene. After complete addition, the mixture was refluxed eight hours, cooled to room temperature, the amine hydrochloride filtered off, and toluene and unreacted amine were removed under reduced pressure. The thick material that resulted was dissolved in hot ethanol and the product was crystallized upon cooling to yield N-sec-butyl-2,6-dinitro-4-t-butylaniline melting at 60°-62° C.

Workup

  1. additiondropwise to a refluxing mixture of 50 ml
  2. additionAfter complete addition
  3. temperaturethe mixture was refluxed eight hours
  4. filtrationthe amine hydrochloride filtered off
  5. customtoluene and unreacted amine were removed under reduced pressure
  6. customThe thick material that resulted
  7. customthe product was crystallized
  8. temperatureupon cooling

Sources & evidence

ORD record
ord-004670f806634018a60582da6d3ee82c
Source dataset
uspto-grants-1978_03
Patent number
US04077795

Reaction notes

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