Ammonia → (2-Fluoro-4-iodophenyl)-urea

HRID 75671Notes

Reaction equation

HRID 75671 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.C1N=C[N:19]([C:22](N2C=NC=C2)=[O:23])C=1.N>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:22]([NH2:19])=[O:23]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 59717008(2-Fluoro-4-iodophenyl)-ureaYield 99.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under argon atmosphere, to a solution of 2-fluoro-4-iodoaniline 47 (20.0 g) and triethylamine (23.6 ml) in chloroform (200 ml) was added N,N-carbonyldiimidazole (27.4 g) with stirring under ice-cooling. After the completion of the addition, the mixture was stirred under ice-cooling for 15 min and at room temperature for 4 hrs. The reaction mixture was ice-cooled, and 28% aqueous ammonia (100 ml) was added dropwise. The mixture was stirred at room temperature for 1.5 hrs. The precipitated crystals were collected by filtration, washed with water and dried to give (2-fluoro-4-iodophenyl)-urea 78 (23.5 g, yield 98.8%) as pale-pink crystals.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the addition
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooled
  5. stirringThe mixture was stirred at room temperature for 1.5 hrs
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-1119a16101b7498aae2428e3708d1f6c
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

Loading…