Hydrogen Peroxide → HCID 54757213, compound

HRID 1782130Notes

Reaction equation

HRID 1782130 reaction equation
[C:1]([C:3]1[C:4]([CH3:14])=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:13])[CH2:10][CH2:11][CH3:12])#[N:2].[OH:15]O>[NH4+].[OH-]>[C:9]([NH:8][C:7]1[S:6][N:5]=[C:4]([CH3:14])[C:3]=1[C:1]([NH2:2])=[O:15])(=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 57587941N-(4-Cyano-3-methyl-1,2-thiazol-5-yl)butanamide

Product 1

HCID 54757213HCID 54757213, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-cyano-3-methyl-isothiazol-5-yl)-butyramide (method 5) (4.18 g, 20 mmol) in 30% aqueous NH4OH (250 mL), was added dropwise 100 mL of hydrogen peroxide at r.t. After the completion of the addition the reaction mixture was stirred at 60° C. overnight after which the TLC showed the complete disappearance of SM. The reaction mixture was cooled and extracted with chloroform (3×100 mL). The organic layer was dried (Na2SO4) and concentrated to get the pure 5-butyrylamino-3-methyl-isothiazole-4-carboxylic acid amide (2.9 g, 72%) as a white solid. 1H NMR (300 MHz) δ 1.03 (t, 3H), 1.79 (m, 2H), 2.54 (t, 3H), 2.69 (s, 3H), 5.97 (bs, 2H), 11.78 (bs, 1H).

Workup

  1. additionAfter the completion of the addition the reaction mixture
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with chloroform (3×100 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e9cc2fe68a73465a8617c117e76ea606
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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