Iodine chloride → HCID 13823541, compound

HRID 1906514Notes

Reaction equation

HRID 1906514 reaction equation
[I:1]Cl.[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=1>CO.C(O)(=O)C>[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][C:5]=1[I:1]

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 650524-Hydroxybenzamide

Product 1

HCID 13823541HCID 13823541, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A sample of 47 g (0.29 mole) of ICl was added to a solution of 40 g (0.29 mole) of 4-hydroxybenzamide in 400 ml of MeOH and 800 ml of acetic acid in the absence of light. The mixture was stirred for 70 hr under N2 at 25° C. A precipitate was collected by filtration. The filtrate was diluted with water and a second crop of crystals collected by filtration. A third crop was obtained by evaporation of solvent from the second filtrate. The combined solids were recrystallized from 95% ethanol. The solid which precipitated and was collected (28 g). It was largely diiodinated material. The filtrate was evaporated in vacuo and the residue recrystallized from MeOH. The precipitated solid was collected by filtration (2.0 g). It was again diiodinated material. The filtrate was concentrated to dryness in vacuo to give 23 g (30% yield) of brownish crystalline 4-hydroxy-3-iodobenzamide, mp 90°-95° C.

Workup

  1. filtrationA precipitate was collected by filtration
  2. additionThe filtrate was diluted with water
  3. filtrationa second crop of crystals collected by filtration
  4. customA third crop was obtained by evaporation of solvent from the second filtrate
  5. customThe combined solids were recrystallized from 95% ethanol
  6. customThe solid which precipitated
  7. customwas collected (28 g)
  8. customThe filtrate was evaporated in vacuo
  9. customthe residue recrystallized from MeOH
  10. filtrationThe precipitated solid was collected by filtration (2.0 g)
  11. concentrationThe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-a8dbf8c622f847c28bb1149c43b70a02
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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