N-bromobutanimide → HCID 22397189, compound

HRID 411190Notes

Reaction equation

HRID 411190 reaction equation
[CH3:1][C:2]1[S:16][C:5]2=[N:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9](=[O:10])[N:4]2[CH:3]=1.C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:24][CH2:1][C:2]1[S:16][C:5]2=[N:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9](=[O:10])[N:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7540596HCID 7540596, compound

Product 1

HCID 22397189HCID 22397189, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 2-methyl-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate (Preparation 8, 1.19 g), NBS (1.07 g) and benzoyl peroxide (25 mg) is heated to reflux in carbon tetrachloride (50 mL) for 6 h. After the mixture is cooled to rt, the precipitate is filtered. The precipitate is re-dissolved in methylene chloride (100 mL) and washed with water. The organic layer is separated, dried (MgSO4), and concentrated to afford 1.0 g (60%) of the title compound as a pale yellow solid. Physical characteristics: MS (ESI+) m/z 317, 319 (M+H)+. 1H NMR (CDCl3)δ 9.80, 8.15, 4.42, 1.40.

Workup

  1. temperatureis heated
  2. filtrationthe precipitate is filtered
  3. dissolutionThe precipitate is re-dissolved in methylene chloride (100 mL)
  4. washwashed with water
  5. customThe organic layer is separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d95c7ee0c7164360953746f899e587ee
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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