Hydroxyamine hydrochloride → HCID 22063863, compound

HRID 1828205Notes

Reaction equation

HRID 1828205 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:15](=O)[C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[C:13]#[N:14])=[CH:11][C:6]=2[N:5]([CH2:24][CH3:25])[C:4]1=[O:26])[CH3:2].Cl.[NH2:28][OH:29]>N1C=CC=CC=1>[NH2:14][C:13]1[O:29][N:28]=[C:15]([C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[C:12]=1[C:10]1[CH:9]=[CH:8][C:7]2[N:3]([CH2:1][CH3:2])[C:4](=[O:26])[N:5]([CH2:24][CH3:25])[C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22063900HCID 22063900, compound

Product 1

HCID 22063863HCID 22063863, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
30 °C

Procedure

To a pyridine (1.5 mL) solution of 2-(1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-oxo-3-m-tolyl-propionitrile (0.113 g) at 23° C. was added hydroxylamine hydrochloride (0.071 g). The reaction was heated to 30° C. for 1 hour then to 55° C. for 3 hours, cooled and extracted into ethyl acetate from 10% citric acid. The organic layer was dried over sodium sulfate and concentrated. The resulting powder was triturated with methanol and filtered to give 5-(5-Amino-3-m-tolyl-isoxazol-4-yl)-1,3-diethyl-1,3-dihydro-benzoimidazol-2-one (0.085 g).

Workup

  1. temperaturecooled
  2. extractionextracted into ethyl acetate from 10% citric acid
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting powder was triturated with methanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5c5aba9a312d4e25876b7d9b5e4db836
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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