Iodine → HCID 14628034, compound

HRID 1199106Notes

Reaction equation

HRID 1199106 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C:10](=O)[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:13][C:14]([NH2:16])=[S:15].II.[OH-].[Na+]>O>[CH:1]1([CH2:7][CH2:8][C:9]2[S:15][C:14]([NH2:16])=[N:13][C:10]=2[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 135556845-Cyclohexylpentan-2-one

Product 1

HCID 14628034HCID 14628034, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 22.2 g of 5-cyclohexyl-2-pentanone, 20.10 g of thiourea, and 33.48 g of iodine was stirred for 23 hours at a bath temperature of from 100° to 120° C. To the mixture was added 150 ml of water, followed by refluxing for 30 minutes. After cooling, an aqueous sodium hydroxide solution was added to neutralize. The mixture was extracted with ethyl acetate, and the extract was washed with water and dried. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography. Recrystallization from aqueous methanol yielded 10.9 g of the titled compound.

Workup

  1. temperatureby refluxing for 30 minutes
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. customdried
  6. customThe solvent was removed by distillation
  7. customthe residue was purified by silica gel column chromatography
  8. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-a32e06e5b0a64903932cdc0e84df2386
Source dataset
uspto-grants-1990_02
Patent number
US04898943

Reaction notes

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