Iodine → HCID 14651914, compound

HRID 2351854Notes

Reaction equation

HRID 2351854 reaction equation
CO.C(=O)([O-])[O-].[K+].[K+].[NH2:9][C:10]([CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:11][C:12](=[S:14])[NH2:13].II>CCOCC.O>[NH2:13][C:12]1[S:14][N:9]=[C:10]([CH2:15][O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 807Iodine2×HCID 887MethanolHCID 11430Potassium CarbonateHCID 72738199HCID 72738199, compound

Product 1

HCID 14651914HCID 14651914, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

In a stream of argon, 182 ml of dry methanol, 191 ml of dry ether and 38.5 g (0.279 mole) of potassium carbonate were added to 31.0 g (0.140 mole) of 3-amino-4-benzyloxy-2-butenethioamide obtained in Referential Example 4, and under heating and reflux, a solution of 26.6 g (0.209 mole) of iodine in dry ether 191 ml was added droopwise to the mixture. Then, the mixture was refluxed for 1.5 hours, and 130 ml of dry ether containing 17.7 g (0.140 mole) of iodine was added dropwise under reflux. After cooling, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water, an aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting 5-amino-3-benzyloxymethyl isothiazole was subjected to silica gel column chromatography, and the column was eluted with chloroform/methanol (500/2) to give 25.5 g (83.0%) of a brown oily substance.

Workup

  1. customobtained in Referential Example 4
  2. temperatureunder heating
  3. temperaturereflux
  4. temperatureThen, the mixture was refluxed for 1.5 hours
  5. temperatureunder reflux
  6. temperatureAfter cooling
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe ethyl acetate layer was washed successively with water
  9. dry with materialan aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. washthe column was eluted with chloroform/methanol (500/2)
  12. customto give 25.5 g (83.0%) of a brown oily substance

Sources & evidence

ORD record
ord-7c7a04c8cfad412699985a65777b9a7d
Source dataset
uspto-grants-1989_10
Patent number
US04874760

Reaction notes

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