2,6-Dichloro-4-nitroaniline → HCID 23036559, compound

HRID 1709698Notes

Reaction equation

HRID 1709698 reaction equation
S(Cl)([Cl:4])(=O)=O.Cl[C:7]1[CH:12]=C([N+]([O-])=O)C=[C:9]([Cl:16])[C:8]=1N1C=CC=C1.[Cl:22][C:23]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[C:26]([Cl:33])[C:24]=1[NH2:25].COC1CCC(OC)O1.C(=O)(O)[O-].[Na+]>CCOCC>[Cl:16][C:9]1[N:25]([C:24]2[C:23]([Cl:22])=[CH:29][C:28]([N+:30]([O-:32])=[O:31])=[CH:27][C:26]=2[Cl:33])[C:12]([Cl:4])=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 74302,6-Dichloro-4-nitroanilineHCID 24648Sulfuryl chlorideHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 620617HCID 620617, compound

Product 1

HCID 23036559HCID 23036559, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sulfuryl chloride (4.68 g, 2.80 ml, 34.7 mmol) is added dropwise to 1-(2,6-dichloro-4-nitrophenyl)pyrrole (4.46 g, 17.4 mmol), prepared from 2,6-dichloro-4-nitroaniline and 2,5-dimethoxytetrahydrofuran following Example 12 procedures, in 20 ml of ether at 0°. After addition is completed, the mixture is stirred at RT for 60 hours. The reaction mixture is then poured into saturated aqueous sodium bicarbonate and extracted with ether. The combined organic layers are washed with brine, dried and stripped of solvent. The residue is purified by prep. TLC to give 2,5-dichloro-1-(2,6-dichloro-4-nitrophenyl)pyrrole, which is reduced with 16% aq. titanium(III) chloride to give 3,5-dichloro-4-(2,5-dichloro-1-pyrrolyl)aniline.

Workup

  1. additionAfter addition
  2. extractionextracted with ether
  3. washThe combined organic layers are washed with brine
  4. customdried
  5. customThe residue is purified by prep

Sources & evidence

ORD record
ord-c48ea3a39766473cb70c6599afeadc61
Source dataset
uspto-grants-1990_08
Patent number
US04950678

Reaction notes

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