Hydrogen iodide → HCID 13644526, compound

HRID 482694Notes

Reaction equation

HRID 482694 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[C:10]1([CH2:17][C:18]([O:20]CC)=[O:19])[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]1.I>O>[Cl:9][C:6]1[CH:5]=[C:4]2[C:10]3([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]3)[CH2:17][C:18](=[O:19])[O:20][C:3]2=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 20244914HCID 20244914, compound

Product 1

HCID 13644526HCID 13644526, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.0 g. (0.0122 mole) of 4-(2'-methoxy-5'-chlorophenyl)-4-(carboethoxymethyl)imidazolidine 2,5-dione in 40 ml. of 58% hydriodic acid was heated to 115° C. for 4 hours. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The combined extracts were washed with a sodium bisulfite solution, water and brine, dried over magnesium sulfate and concentrated in vacuo to dryness. The residue was chromatographed using ethyl acetatehexane as the eluent (1:1; V:V) to give 106 mg. of product as the less polar material, m.p. 289°-290° C. (dec.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with a sodium bisulfite solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was chromatographed
  7. customto give 106 mg

Sources & evidence

ORD record
ord-19bfbb3b3fa04c0c9ebe652046cc2cb4
Source dataset
uspto-grants-1986_03
Patent number
US04575507

Reaction notes

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