Hydrogen Bromide → HCID 10665811, compound

HRID 1709323Notes

Reaction equation

HRID 1709323 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24]CC5C=CC=CC=5)=[CH:20][CH:19]=4)=[N:14][C:13]=3[CH:32]=2)[S:3]1.Br.C(OCC)(=O)C.O>C(O)(=O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)=[N:14][C:13]=3[CH:32]=2)[S:3]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 8857Ethyl AcetateHCID 14674504HCID 14674504, compound

Product 1

HCID 10665811HCID 10665811, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 0.95 g of 5-[(2,4-dioxothiazolidin-5-yl)methyl)-2-(4-benzyloxybenzyl)benzoxazole, 10 ml of a 25% hydrogen bromide solution in acetic acid and 10 ml of acetic acid is stirred at room temperature overnight. Ethyl acetate and water are added to the reaction mixture. The ethyl acetate layer is washed with water, dried and evaporated to remove the solvent. The residue is crystallized with n-hexane, and recrystallized from a mixture of ethyl acetate and n-hexane, whereby 0.42 g of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-(4-hydroxybenzyl)benzoxazole is obtained as colorless needles.

Workup

  1. washThe ethyl acetate layer is washed with water
  2. customdried
  3. customevaporated
  4. customto remove the solvent
  5. customThe residue is crystallized with n-hexane
  6. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-aa2df4e7777c4ac9949f7f2570e6f686
Source dataset
uspto-grants-1990_08
Patent number
US04948900

Reaction notes

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