Water → HCID 18327528, compound

HRID 636666Notes

Reaction equation

HRID 636666 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH2:7][OH:8].C(N(CC)CC)C.[C:16](Cl)(=[O:20])[O:17][CH2:18][CH3:19].O>O1CCCC1>[C:16](=[O:20])([O:8][CH2:7][C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])[O:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18411623(4-Methyl-1,2,3-thiadiazol-5-yl)methanol

Product 1

HCID 18327528HCID 18327528, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran was dissolved 0.50 g (3.8 mmol) of 4-methyl-1,2,3-thiadiazol-5-ylmethanol. After adding 0.80 g (7.6 mmol) of triethylamine and 0.60 g (5.7 mmol) of ethyl chlorocarbonate, the resulting mixture was stirred at room temperature for 22 hours. Then, water was added to the reaction mixture to stop the reaction, the objective product was extracted with ethyl acetate, the organic layer was washed with water and dried, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 5:1 mixture of n-hexane and ethyl acetate. Thus, 0.50 g of the objective compound was obtained.

Workup

  1. customthe reaction
  2. extractionthe objective product was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. addition5:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-d296aa72cdc04c3fafffd92830ea5762
Source dataset
uspto-grants-2001_02
Patent number
US06194444B1

Reaction notes

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