1H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dione → HCID 18393042, compound

HRID 1739517Notes

Reaction equation

HRID 1739517 reaction equation
[CH2:1]([C:3]1[S:7][C:6](=[NH:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[N:4]=1)[CH3:2].[C:17]12[C:25](=[O:26])[O:24][C:22](=[O:23])[C:18]=1[CH2:19][CH2:20][CH2:21]2>C(Cl)(Cl)Cl.C(OCC)C>[CH2:1]([C:3]1[S:7][C:6](=[N:8][C:25]([C:17]2[CH2:21][CH2:20][CH2:19][C:18]=2[C:22]([OH:24])=[O:23])=[O:26])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 3248541H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dioneHCID 21840881HCID 21840881, compound

Product 1

HCID 18393042HCID 18393042, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 5-ethyl-2-imino-3-(4-iodobenzyl)-1,3,4-thiadiazoline (17.3 g) in chloroform (200 ml) was added 1-cyclopentene-1,2-dicarboxylic anhydride (7.5 g), and they were stirred at room temperature for one hour. The reaction mixture was washed with 1N hydrochloric acid and dried over anhydrous magnesium sulfate, followed by removal through distillation. The residue so obtained was dispersed in diethyl ether and collected by filtration, whereby 23.8 g of the title compound was obtained.

Workup

  1. washThe reaction mixture was washed with 1N hydrochloric acid
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customfollowed by removal through distillation
  4. customThe residue so obtained
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7973608d2dfc4cfbb409bf1321269e0c
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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