Toluene → Butralin

HRID 1730109Notes

Reaction equation

HRID 1730109 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>[C:10]([C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([NH:22][CH:18]([CH2:20][CH3:21])[CH3:19])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=1)([CH3:13])([CH3:12])[CH3:11]

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

1 gram of 2,6-dinitro-4-tert-butylchlorobenzene was allowed to react with 1 gram of sec-butylamine by adding the amine dropwise to a refluxing mixture of 50 ml. dry toluene, and the 2,6-dinitro-4-tert-butylchlorobenzene. After complete addition, the mixture was refluxed 8 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 4-tert-butyl-N-sec-butyl-2,6 -dinitroaniline melting at 60° -62° C.

Workup

  1. additiondropwise to a refluxing mixture of 50 ml
  2. additionAfter complete addition
  3. temperaturethe mixture was refluxed 8 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-ac6c2972e0c74d9ab85325d13136f040
Source dataset
uspto-grants-1976_11
Patent number
US03991116

Reaction notes

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