Methanesulfonyl chloride → HCID 15729206, compound

HRID 1657005Notes

Reaction equation

HRID 1657005 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][N:6]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:14][S:15]([NH:1][C:2]1[S:3][C:4]([S:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][N:6]=1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15729159HCID 15729159, compound

Product 1

HCID 15729206HCID 15729206, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-(2-pyrimidinylthio)thiazole (1.0 g) in a pyridine (20 ml) was dropwise added methanesulfonyl chloride (0.8 ml) at 5° C. with stirring. The mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure and water was added to this residue. The mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1), washed with aqueous saturated sodium chloride and dried over magnesium sulfate. The solution was concentrated under reduced pressure to give solid. The solid was recrystallized from 50% ethanol to give 2-methanesulfonylamino-5-(2-pyrimidinylthio)thiazole (0.60 g, yield: 43.8%). mp: 200° C. (dec.) IR (Nujol): 3120, 1585, 1545, 1440, 1305, 1140 cm-1

Workup

  1. customat 5° C.
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure and water
  4. additionwas added to this residue
  5. extractionThe mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  6. washwashed with aqueous saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated under reduced pressure
  9. customto give solid
  10. customThe solid was recrystallized from 50% ethanol

Sources & evidence

ORD record
ord-ca661e29d0ad46669c4d9db30f576201
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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