Iodine chloride → HCID 21285517, compound

HRID 2231649Notes

Reaction equation

HRID 2231649 reaction equation
[I:1]Cl.[NH2:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:3][C:4]1[CH:17]=[CH:16][C:15]([I:1])=[CH:14][C:5]=1[CH2:6][NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 21285528HCID 21285528, compound

Product 1

HCID 21285517HCID 21285517, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodine monochloride (3.24 g) was added to a stirred solution of ethyl N-(2-aminobenzyl)glycinate (4.16 g) (see U.S. Pat. No. 3,983,120) and sodium acetate (1.804 g) in acetic acid (100 cm3) at room temperature. After 1 hour volatile material was removed in vacuo and the residue was partitioned between chloroform (200 -cm3) and saturated aqueous sodium carbonate solution (50 cm3). The aqueous phase was further extracted with chloroform (2×50 cm3) and the combined organic extracts were washed with 10% aqueous sodium thiosulphate solution (50 cm3). The dried (MgSO4) organic extracts were evaporated in vacuo and the oily residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting witb chloroform. Combination and evaporation of the appropriate fractions gave a solid (4.9 g), a small portion of which was recrystallised from hexane-ethyl acetate to afford the title compound, m.p. 58°-61°.

Workup

  1. customat room temperature
  2. customAfter 1 hour volatile material was removed in vacuo
  3. customthe residue was partitioned between chloroform (200 -cm3) and saturated aqueous sodium carbonate solution (50 cm3)
  4. extractionThe aqueous phase was further extracted with chloroform (2×50 cm3)
  5. washthe combined organic extracts were washed with 10% aqueous sodium thiosulphate solution (50 cm3)
  6. dry with materialThe dried (MgSO4) organic extracts
  7. customwere evaporated in vacuo
  8. customthe oily residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  9. washeluting witb chloroform
  10. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-2cfc83f255154752a8a50938aedaba7a
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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