Urea → 4-chloro-1-iodo-2-nitrobenzene

HRID 1030435Notes

Reaction equation

HRID 1030435 reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[CH:11][C:9](N)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1.NC(N)=O.[I-:20].[K+]>Cl>[N+:13]([C:8]1[CH:7]=[C:6]([Cl:5])[CH:12]=[CH:11][C:9]=1[I:20])([O-:15])=[O:14]

Participants

6

Reactant 4

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

Product 1

HCID 2265664-chloro-1-iodo-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A 1M aqueous solution of sodium nitrite (50 milliliters (mL)) was added dropwise to a cold (3° C.) stirred mixture of 4-chloro-2-nitroaniline (8.63 grams (g), 50 millimoles (mmol)) in 6M HCl (150 mL) over a 45 minute (min) period with subsequent addition of about 5 g of urea during 30 min. An aqueous solution of potassium iodide (60 mL, 1M) was dripped into the resulting orange solution over a period of 35 min at 5° C. After an additional 45 min, the desired product, which had separated from solution, was isolated by filtration and then dried in air; yield, 13.73 g (brown powder): m.p. 50°-60° C.

Workup

  1. customthe desired product, which had separated from solution
  2. customwas isolated by filtration
  3. customdried in air
  4. customyield

Sources & evidence

ORD record
ord-29abea20a419433b8ff3b75785340d12
Source dataset
uspto-grants-1992_04
Patent number
US05106407

Reaction notes

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