Catechol → Spiro[1,3-benzodioxole-2,2'-imidazolidine]-4',5'-dione

HRID 1834110Notes

Reaction equation

HRID 1834110 reaction equation
[N:1]#[C:2][NH2:3].[C:4](Cl)(=[O:8])[C:5](Cl)=[O:6].[C:10]1([C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13])[OH:11]>O1CCOCC1>[NH:1]1[C:5](=[O:6])[C:4](=[O:8])[NH:3][C:2]21[O:13][C:12]1[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=1[O:11]2

Participants

5

Reactant 3

HCID 289CatecholHCID 9864CyanamideHCID 65578Oxalyl chloride

Product 1

HCID 20374006Spiro[1,3-benzodioxole-2,2'-imidazolidine]-4',5'-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.155 mol (6.5 g) of dehydrated cyanamide were put into 500 ml of anhydrous dioxane and 0.155 mol (19.65 g) of oxalyl chloride were added dropwise at 20° C. After 2 hours' stirring, 0.155 mol (17.1 g) of pyrocatechol, dissolved in 50 ml of dioxane, were added dropwise. The reaction mixture was stirred overnight, suction filtered to remove precipitate and washed with dioxane and water. The solid product was dried and stirred up with about 200 ml of acetone, filtered with Tonsil and evaporated to dryness under reduced pressure at a bath temperature of about 35° C. 13.2 g, which is 41.4% of the theoretical yield, of spiro-[1,3-benzodioxol-2,2'-imidazolidine]-4',5'-dione were obtained. The melting point was 202° C with decomposition.

Workup

  1. additionwere added dropwise at 20° C
  2. additionwere added dropwise
  3. stirringThe reaction mixture was stirred overnight
  4. filtrationsuction filtered
  5. customto remove precipitate
  6. washwashed with dioxane and water
  7. customThe solid product was dried
  8. stirringstirred up with about 200 ml of acetone
  9. filtrationfiltered with Tonsil
  10. customevaporated to dryness under reduced pressure at a bath temperature of about 35° C

Sources & evidence

ORD record
ord-87e90123c0694ffa9ad4dbfa8d6ac90b
Source dataset
uspto-grants-1978_01
Patent number
US04069052

Reaction notes

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