Iodine → HCID 14230006, compound

HRID 34551Notes

Reaction equation

HRID 34551 reaction equation
[CH2:1]([N:5]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2([C:12](=[O:13])[NH:11][C:10](=[O:14])[NH:9]2)[N:7]([CH3:21])[C:6]1=[O:22])[CH:2]([CH3:4])[CH3:3].S(Cl)([Cl:26])(=O)=O.II>C(O)(=O)C>[Cl:26][C:17]1[CH:16]=[C:15]2[C:8]3([C:12](=[O:13])[NH:11][C:10](=[O:14])[NH:9]3)[N:7]([CH3:21])[C:6](=[O:22])[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:20]2=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 807IodineHCID 24648Sulfuryl chlorideHCID 14230005HCID 14230005, compound

Product 1

HCID 14230006HCID 14230006, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Isobutyl-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (0.76 g) as prepared in Example 37 is suspended in acetic acid (15 ml) and thereto are added sulfuryl chloride (0.3 ml) and a slight amount of iodine, and the mixture is stirred at room temperature for 19 hours. The reaction mixture is poured into ice-water, and the precipitates are taken by filtration and the crystals are dissolved in 10% aqueous sodium hydroxide. The undissolved materials are filtered off, and the filtrate is neutralized with 10% hydrochloric acid, and the precipitates are taken by filtration (this dissolution and precipitation procedure is repeated). The precipitates are taken by filteration and dried to give 6-chloro-1-isobutyl-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (0.45 g).

Workup

  1. filtrationthe precipitates are taken by filtration
  2. dissolutionthe crystals are dissolved in 10% aqueous sodium hydroxide
  3. filtrationThe undissolved materials are filtered off
  4. filtrationthe precipitates are taken by filtration (
  5. dissolutionthis dissolution and precipitation procedure
  6. customdried

Sources & evidence

ORD record
ord-33c5b8a1419048b1887f83eaa261aff4
Source dataset
uspto-grants-1988_08
Patent number
US04762839

Reaction notes

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