Sodium Chloride → HCID 18327517, compound

HRID 1250197Notes

Reaction equation

HRID 1250197 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH2:7][OH:8].[C:9](Cl)(=[O:11])[CH3:10].C(N(CC)CC)C.[Cl-].[Na+]>O1CCCC1>[C:9]([O:8][CH2:7][C:6]1[S:5][N:4]=[N:3][C:2]=1[CH3:1])(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18411623(4-Methyl-1,2,3-thiadiazol-5-yl)methanol

Product 1

HCID 18327517HCID 18327517, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran were dissolved 0.50 g (3.8 mmol) of 4-methyl-1,2,3-thiadiazol-5-ylmethanol, 0.50 g (5.7 mmol) of acetyl chloride and 0.80 g (7.6 mmol) of triethylamine. The solution thus obtained was stirred at room temperature for 18 hours. Then, a saturated aqueous solution of sodium chloride 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 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.70 g of the objective compound was obtained.

Workup

  1. customThe solution thus obtained
  2. customthe reaction
  3. extractionthe objective product was extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. customdried
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. addition3:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-1beda3e6b0734d86bd4347b53fa3a1b5
Source dataset
uspto-grants-2002_01
Patent number
US06337341B1

Reaction notes

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