Reaction #5881

ord-269df9c1e534472b9cb72738c8208fee

Reaction equation

O
water
CC(C)(C)c1nc2cc(Cl)c([N+](=O)[O-])cc2s1
2-tert-butyl-5-chloro-6-nitrobenzothiazole
CC1CCNCC1
4-methylpiperidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CC1CCN(c2cc3nc(C(C)(C)C)sc3cc2[N+](=O)[O-])CC1
2-tert-butyl-5-(4-methylpiperidin-1-yl)-6-nitrobenzothiazole

Reactants

O
water
CC(C)(C)c1nc2cc(Cl)c([N+](=O)[O-])cc2s1
2-tert-butyl-5-chloro-6-nitrobenzothiazole
CC1CCNCC1
4-methylpiperidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagents

None

Solvents

ClC(Cl)Cl
chloroform
CS(C)=O
dimethylsulphoxide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooled
  2. 2
    OtherThe solid obtained
  3. 3
    Filtrationfiltered through a silical gel column
  4. 4
    OtherThe filtate is evaporated

Procedure

A solution of 32,4 g of 2-tert-butyl-5-chloro-6-nitrobenzothiazole, (described in European patent application 85810418.5 published under No. 0175650) in 300 ml of dimethylsulphoxide, is stirred and heated at 140° for 6 hours with 12.8 g of 4-methylpiperidine and 35.8 g of anhydrous potassium carbonate, cooled and poured into water. The solid obtained is dissolved in chloroform and filtered through a silical gel column. The filtate is evaporated to give 2-tert-butyl-5-(4-methylpiperidin-1-yl)-6-nitrobenzothiazole melting at 116°-120°.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246927uspto-grants-1993_09