Epichlorohydrin → HCID 13823542, compound

HRID 1906515Notes

Reaction equation

HRID 1906515 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[I:11].[H-].[Na+].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>CN(C=O)C>[I:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[O:1][CH2:14][CH:16]1[CH2:17][O:18]1)[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 13823541HCID 13823541, compound

Product 1

HCID 13823542HCID 13823542, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 10.0 g (0.038 mole) of 4-hydroxy-3-iodobenzamide in 40 ml of dry DMF was added to a suspension of 0.04 mole of sodium hydride (from 1.9 g of 50% sodium hydride which had been washed free of oil with hexane) in 60 ml of dry DMF at 25° under N2. When bubbling ceased, 30 ml (0.38 mole) of epichlorohydrin was added dropwise. The mixture was heated at 70° C. for 90 min and allowed to stand at 25° C. for 16 hr. The mixture was filtered. The filtrate was concentrated to dryness in vacuo. The residue was dissolved in CH2Cl3. The solution was washed with water and brine, dried (MgSO4) and the solvent evaporated in vacuo. The residue was recrystallized from CH2Cl2 /hexane to give 5.4 g (50% yield) of 3-iodo-4-(oxiranylmethoxy)benzamide, mp 149°-151° C.

Workup

  1. customWhen bubbling
  2. filtrationThe mixture was filtered
  3. concentrationThe filtrate was concentrated to dryness in vacuo
  4. dissolutionThe residue was dissolved in CH2Cl3
  5. washThe solution was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated in vacuo
  8. customThe residue was recrystallized from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-d04d0332577b4f56b57eee946260bae3
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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