Water → HCID 178456349, compound

HRID 1619236Notes

Reaction equation

HRID 1619236 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl.[NH2:22][OH:23].O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:23][NH:22][C:19]([C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]3)[S:11][C:12]=2[CH:18]=1)=[NH:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 237287892-(4-Isopropylpiperazin-1-yl)benzothiazole-6-carbonitrile

Product 1

HCID 178456349HCID 178456349, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carbonitrile (5.0 g, 17.5 mmol) in ethanol (50 mL) was added hydroxylamine hydrochloride (3.6 g, 52.4 mmol), water (8 mL) and potassium carbonate (7.2 g, 52.4 mmol). The reaction mixture was heated overnight at reflux. The mixture was allowed to cool and then concentrated in vacuo. The residue was dissolved into THF (30 mL) and then filtered. The filtrate was concentrated in vacuo to give 4 g of crude N-hydroxy-2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxamidine.

Workup

  1. temperatureThe reaction mixture was heated overnight
  2. temperatureat reflux
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved into THF (30 mL)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9c677b7b54c44bd2970b6a1a09cb9736
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

Loading…