Urea → 4-chloro-1-iodo-2-nitrobenzene

HRID 1601023Notes

Reaction equation

HRID 1601023 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.N([O-])=O.[Na+].NC(N)=O.[I-:20].[K+]>S(=O)(=O)(O)O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([I:20])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

7

Reactant 4

HCID 1176UreaHCID 4875Potassium IodideHCID 69794-Chloro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 2265664-chloro-1-iodo-2-nitrobenzeneYield 93.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 4-chloro-2-nitroaniline (5.18 g) in a 12 N sulphuric acid solution (60 ml) cooled to 10° a solution of sodium nitrite (2.76 g) in sulphuric acid (20 ml) and polyphosphoric acid (40 ml) were sequentially added. The reaction mixture was stirred for 3 hrs at r.t., then poured into crushed ice and urea was added until gas evolution ceases. The resulting solution was treated with an aqueous solution (20 ml) of potassium iodide (7.47 g) and heated at 70° for 1 h. The mixture was diluted with brine and extracted with EA then the organic phase was washed with brine, dried and concentrated in vacuo. The residue was purified by flash column chromatography (CH/EA=100/0 to 95/5 as eluant), obtaining the title compound as yellow solid (7.96 g). m.p. 55-56° C.

Workup

  1. additionwere sequentially added
  2. additionpoured
  3. additionwas added until gas evolution ceases
  4. temperatureheated at 70° for 1 h
  5. extractionextracted with EA
  6. washthe organic phase was washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (CH/EA=100/0 to 95/5 as eluant)

Sources & evidence

ORD record
ord-b23e8eece69e458f9520b233858a14ab
Source dataset
uspto-grants-1999_11
Patent number
US05977136

Reaction notes

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