Water → HCID 21840881, compound

HRID 1739512Notes

Reaction equation

HRID 1739512 reaction equation
[CH2:1]([C:3]1[S:7][C:6](=[N:8]C(=O)C(F)(F)F)[N:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=2)[N:4]=1)[CH3:2].[OH-].[Na+].O>O1CCCC1>[CH2:1]([C:3]1[S:7][C:6](=[NH:8])[N:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18393045HCID 18393045, compound

Product 1

HCID 21840881HCID 21840881, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-ethyl-3-(4-iodobenzyl)-2-trifluoroacetylimino-1,3,4-thiadiazoline (44.1 g) in tetrahydrofuran (300 ml) was added 2N sodium hydroxide (100 ml), followed by stirring at room temperature overnight. Water (300 ml) was added to the reaction mixture, followed by extraction with chloroform (250 ml) twice. The organic layers were washed with a saturated aqueous sodium hydrogencarbonate and were dried over anhydrous magnesium sulfate, followed by removal through distillation. The oily substance so obtained was crystallized from diisopropyl ether, whereby 32.3 g of the title compound was obtained.

Workup

  1. extractionfollowed by extraction with chloroform (250 ml) twice
  2. washThe organic layers were washed with a saturated aqueous sodium hydrogencarbonate
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. customfollowed by removal through distillation
  5. customThe oily substance so obtained
  6. customwas crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-90bc03054ca14f17ba720364a069062c
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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