1-Chloro-2,4-Dinitrobenzene → HCID 18546610, compound

HRID 1281050Notes

Reaction equation

HRID 1281050 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([O:11][CH2:12][C:13]([F:26])([F:25])[C:14]([F:24])([F:23])[C:15]([F:22])([F:21])[C:16]([F:20])([F:19])[CH2:17][OH:18])=[C:5]([F:27])[C:4]=1[F:28].Cl[C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:32]=1[N+:40]([O-:42])=[O:41].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.O>[CH3:1][N:2]([CH3:29])[C:3]1[C:4]([F:28])=[C:5]([F:27])[C:6]([O:11][CH2:12][C:13]([F:26])([F:25])[C:14]([F:23])([F:24])[C:15]([F:21])([F:22])[C:16]([F:19])([F:20])[CH2:17][O:18][C:35]2[CH:36]=[CH:31][C:32]([N+:40]([O-:42])=[O:41])=[CH:33][C:34]=2[N+:37]([O-:39])=[O:38])=[C:7]([F:10])[C:8]=1[F:9]

Participants

6

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 11430Potassium CarbonateHCID 18546604HCID 18546604, compound

Product 1

HCID 18546610HCID 18546610, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N,N-Dimethyl-4-(6-hydroxy-2,2,3,3,4,4,5,5-octafluorohexyloxy)-2,3,5,6-tetrafluorobenzeneamine (1.05 g) was treated with 1-chloro-2,4-dinitrobenzene (0.51 g) and potassium carbonate (0.35 g) in NMP (5 mL) at 80° C. for 21.5 hrs. The mixture was diluted with water and extracted with ethyl ether. The extracts were washed with water and brine, dried (K2CO3), and concentrated to an orange oil. The oil was purified by chromatography to give N,N-dimethyl-4-[6-(2,4-dinitrophenoxy)-2,2,3,3,4,4,5,5-octaflurohexyloxy]-2,3,5,6-tetrafluorobenzeneamine (1.05 g) as an oil.

Workup

  1. extractionextracted with ethyl ether
  2. washThe extracts were washed with water and brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated to an orange oil
  5. customThe oil was purified by chromatography

Sources & evidence

ORD record
ord-4aa71c874f4042deb5727556eac12045
Source dataset
uspto-grants-2002_09
Patent number
US06451960B1

Reaction notes

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