2-Aminothiazole → HCID 9117500, compound

HRID 1828878Notes

Reaction equation

HRID 1828878 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(N(CC)CC)C.[CH2:14]([S:18](Cl)(=[O:20])=[O:19])[CH2:15][CH2:16][CH3:17]>C1COCC1>[CH2:14]([S:18]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)(=[O:20])=[O:19])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 754301-Butanesulfonyl chloride2×

Product 1

HCID 9117500HCID 9117500, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.4 g of 2-aminothiazole (73.7 mmol) and 10.2 ml of triethylamine (7.4 g, 73.7 mmol) were dissolved at room temperature in 100 ml of THF. Again at room temperature 9.6 ml of n-butanesulfonyl chloride (11.5 g, 73.7 mmol) were added dropwise to this solution over the course of one hour. After 21 h of stirring at room temperature a further 4 ml of n-butanesulfonyl chloride (4.8 g, 30.8 mmol) were added and stirring was continued at room temperature for 20 h. The reaction mixture was washed twice with 100 ml of 1 N NaOH and then washed to neutrality (pH 6–7) with water. The organic phase was dried over magnesium sulphate and then freed from the solvent. The 9.0 g of crude product obtained were recrystallized from 80 ml of tert-butyl methyl ether. This gave 3.2 g of the target compound, whose constitution was verified by NMR spectroscopy.

Workup

  1. additionwere added
  2. washThe reaction mixture was washed twice with 100 ml of 1 N NaOH
  3. washwashed to neutrality (pH 6–7) with water
  4. dry with materialThe organic phase was dried over magnesium sulphate

Sources & evidence

ORD record
ord-26bf2e46907c43fab75e5fc1587d91df
Source dataset
uspto-grants-2006_06
Patent number
US07060817B2

Reaction notes

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