Imidazole → HCID 89815242, compound

HRID 2172291Notes

Reaction equation

HRID 2172291 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.[F:7][C:8]1[S:12][C:11]([NH2:13])=[N:10][CH:9]=1.[S:14](Cl)(Cl)(=[O:16])=[O:15]>C(Cl)Cl.CCCCCCC>[F:7][C:8]1[S:12][C:11]([NH:13][S:14]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)(=[O:16])=[O:15])=[N:10][CH:9]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24648Sulfuryl chlorideHCID 118589315-Fluoro-1,3-thiazol-2-amine hydrochloride

Product 1

HCID 89815242HCID 89815242, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

A solution of 1H-imidazole (6.17 g, 91 mmol) and 5-fluorothiazol-2-amine hydrochloride (Milestone Pharmatech, Brunswick, N.J., 3.50 g, 22.64 mmol) in 100 mL DCM was cooled to −78° C. sulfuryl chloride (1.841 ml, 22.64 mmol) was added, and the reaction mixture was allowed to stir for 10 minutes. The reaction mixture was then transferred to a 0° C. cooling bath, and was allowed to stir for an additional hour. LC/MS showed mostly product, so the reaction mixture was diluted with a small amount of heptane, and the solvent was decanted off. The resulting solid was dried (kept under vacuum) and used without further purification. [M+H]+=249.0

Workup

  1. additionwas added
  2. customwas then transferred to a 0° C.
  3. temperaturecooling bath
  4. stirringto stir for an additional hour
  5. customthe solvent was decanted off
  6. customThe resulting solid was dried (kept under vacuum)
  7. customused without further purification

Sources & evidence

ORD record
ord-07c4588b7aa0425eb7072f463d0c4bba
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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