Iodine chloride → (2-Amino-5-iodophenyl) (2-chlorophenyl)methanone

HRID 1032746Notes

Reaction equation

HRID 1032746 reaction equation
[I:1]Cl.[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:11]>C(Cl)Cl>[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([I:1])=[CH:6][C:5]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:11]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 761652-Amino-2'-chlorobenzophenone

Product 1

HCID 14851954(2-Amino-5-iodophenyl) (2-chlorophenyl)methanoneYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine monochloride, 15 ml (21 g), was added to a solution of 23 g (0.1 mol) of (2-aminophenyl)(2 chlorophenyl)methanone [ref. E. Reeder and L. H. Sternbach, U.S. Pat. No. 3,371,085; February 1968] in 500 ml of methylene chloride cooled to -60° C. After stirring with cooling for 5 hours, the cooling bath was removed and the temperature of the reaction mixture was allowed to reach 0° C. Following the addition of 300 ml of aqueous sodium bisulfite solution, the two phase system was stirred for 10 minutes. The organic phase was separated, dried over sodium sulfate and evaporated. The residue was crystallized from ether/hexane to yield 20 g (56%) of (2-amino-5-iodophenyl) (2-chlorophenyl)methanone with m.p. 120°-122° C.

Workup

  1. temperaturewith cooling for 5 hours
  2. customthe cooling bath was removed
  3. customto reach 0° C
  4. additionthe addition of 300 ml of aqueous sodium bisulfite solution
  5. stirringthe two phase system was stirred for 10 minutes
  6. customThe organic phase was separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-5eecce3a3c2a4d7d938137c4e0bff883
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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