Hydrogen Peroxide → HCID 54757315, compound

HRID 1782141Notes

Reaction equation

HRID 1782141 reaction equation
[C:1]([C:3]1[C:4]([CH3:15])=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12])#[N:2].[OH:16]O>[NH4+].[OH-]>[CH3:15][C:4]1[C:3]([C:1]([NH2:2])=[O:16])=[C:7]([NH:8][C:9](=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12])[S:6][N:5]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 54757314N-(4-Cyano-3-methyl-1,2-thiazol-5-yl)-3-methylbutanamide

Product 1

HCID 54757315HCID 54757315, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-cyano-3-methyl-isothiazol-5-yl)-3-methyl-butyramide (method 24) (8 g, 35.8 mmol) in 30% aqueous NH4OH (200 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 concentrated to 40 mL and extracted with chloroform (3×100 mL). The organic layer was dried (Na2SO4) and concentrated to obtain 3-methyl-5-(3-methyl-butyrylamino)-isothiazole-4-carboxylic acid amide (6.1 g, 71%) as a light yellow solid. 1H NMR (300 MHz) δ 1.03 (d, 6H), 2.24 (m, 1H), 2.43 (d, 2H), 2.69 (s, 3H), 5.98 (bs, 2H), 11.77 (bs, 1H).

Workup

  1. additionAfter the completion of the addition the reaction mixture
  2. concentrationThe reaction mixture was concentrated to 40 mL
  3. extractionextracted with chloroform (3×100 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dcce0b8578ac45eab9f0f98071258bd7
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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