4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 86746622, compound

HRID 1613796Notes

Reaction equation

HRID 1613796 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][OH:9].[S:10](Cl)(=[O:13])(=[O:12])[NH2:11].[CH2:15](N(CC)CC)C>C(#N)C>[CH3:15][CH:8]([OH:9])[CH3:7].[OH2:12].[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][O:9][S:10](=[O:13])(=[O:12])[NH2:11]

Participants

5

Reactant 3

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 8471TriethylamineHCID 24499Chlorosulfamic acid

Product 1

HCID 86746622HCID 86746622, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methyl-5-thiazoleethanol (10.0 g, 0.0698 mole) was dissolved in acetonitrile, chilled, and sulfamoyl chloride (10.44 g, 0.091 mole) was added to the stirred solution. Triethylamine (9.19 g, 0.091 mole) was added dropwise while maintaining the temperature between 20°-25° C. A yellow solid precipitated after the addition was completed. The reaction was stirred at room temperature overnight, evaporated to a residue, and the residue partitioned between ethyl acetate/acetonitrile (1:1) and sodium bicarbonate/sodium chloride (1:1). The organic phase was treated with charcoal, dried (magnesium sulfate), filtered, and evaporated to a residue (9.29 g). The residue was dissolved in a small amount of methanol and isopropanol was added. The first crop (2.0 g) crystallized out of isopropanol as the methanol was evaporated. The crystals were collected and dried to yield 2.0 g (13%) of solid, mp 80°-83° C.

Workup

  1. temperaturechilled
  2. temperaturewhile maintaining the temperature between 20°-25° C
  3. customA yellow solid precipitated
  4. additionafter the addition
  5. customevaporated to a residue
  6. customthe residue partitioned between ethyl acetate/acetonitrile (1:1) and sodium bicarbonate/sodium chloride (1:1)
  7. additionThe organic phase was treated with charcoal
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated to a residue (9.29 g)
  11. dissolutionThe residue was dissolved in a small amount of methanol and isopropanol
  12. additionwas added
  13. customThe first crop (2.0 g) crystallized out of isopropanol as the methanol
  14. customwas evaporated
  15. customThe crystals were collected
  16. customdried

Sources & evidence

ORD record
ord-3898812475d947c1bc29fbc4b71f4980
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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