Hexane → 2-Methyl-6-(piperidine-1-sulfonyl)-benzothiazole

HRID 409698

Reaction equation

HRID 409698 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CCCCCC>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)(=[O:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 8082PiperidineHCID 35830192-Methyl-1,3-benzothiazole-6-sulfonyl chloride

Product 1

HCID 10756752-Methyl-6-(piperidine-1-sulfonyl)-benzothiazoleYield 74.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of Compound 2 (2.5 g, 10 mmol) in chloroform (15 ml) was added drop wise to a solution of piperidine (1.7 g, 20.0 mmol) in chloroform (10 ml). The combined mixture was stirred at room temperature for 1 hour. The reaction mixture was then washed with water (2×, 50 ml) and brine (1×, 50 ml). The organic layer was dried with sodium sulfate and evaporated. The sticky white solid thus obtained was dissolved in ca. 5 ml of hot ethyl acetate and this solution was then slowly added to 40 ml hexane. The white solid that precipitated was collected, washed with hexane and dried to yield 2.2 g (74%) of Compound 3, Rf=0.28 (30% ethyl acetate in hexane). The structure of Compound 3 is given below:

Workup

  1. washThe reaction mixture was then washed with water (2×, 50 ml) and brine (1×, 50 ml)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customevaporated
  4. customThe sticky white solid thus obtained
  5. customThe white solid that precipitated
  6. customwas collected
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-5e3b8c719ad04582899ed8877fe21f51
Source dataset
uspto-grants-2014_06
Patent number
US08759526B2

Linked notes

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