Benzoyl chloride → 2-(4-Isopropylpiperazin-1-yl)-6-(5-phenyl-[1,2,4]oxadiazol-3-yl)benzothiazole

HRID 1944664Notes

Reaction equation

HRID 1944664 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)[S:11][C:7]=2[CH:6]=1)=[NH:4].[C:23](Cl)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)(=O)C>[CH:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]2[S:11][C:7]3[CH:6]=[C:5]([C:3]4[N:4]=[C:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[O:1][N:2]=4)[CH:22]=[CH:21][C:8]=3[N:9]=2)[CH2:17][CH2:16]1)([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178456349HCID 178456349, compound

Product 1

HCID 237288252-(4-Isopropylpiperazin-1-yl)-6-(5-phenyl-[1,2,4]oxadiazol-3-yl)benzothiazoleYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-hydroxy-2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxamidine (650 mg, 2.04 mmol) in acetic acid (40 mL) was added benzoylchloride (3 mL). The reaction mixture was stirred overnight at room temperature and then refluxed for 2 h. The reaction mixture was concentrated in vacuo and the residue was dissolved into 0.5 N hydrochloric acid (30 mL). The aqueous solution was extracted with diethyl ether (3×15 mL). The organic layer was discarded and the aqueous phase was basified to pH 13 with 4 N sodium hydroxide and then extracted with ethyl acetate (4×10 mL). The combined organic extracts were evaporated and the residue was recrystallized three times from a mixture of CH2Cl2 and MeOH to give 189 mg (26%) of 2-(4-isopropylpiperazin-1-yl)-6-(5-phenyl-[1,2,4]oxadiazol-3-yl)benzothiazole.

Workup

  1. temperaturerefluxed for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved into 0.5 N hydrochloric acid (30 mL)
  4. extractionThe aqueous solution was extracted with diethyl ether (3×15 mL)
  5. extractionextracted with ethyl acetate (4×10 mL)
  6. customThe combined organic extracts were evaporated
  7. customthe residue was recrystallized three times
  8. additionfrom a mixture of CH2Cl2 and MeOH

Sources & evidence

ORD record
ord-eb5d61ead6e04608a970c78303e5b61c
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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