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

HRID 2099871Notes

Reaction equation

HRID 2099871 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-8290c4aa411e41a8ad7e63f6d5770292
Source dataset
uspto-grants-2009_08
Patent number
US07569695B2

Reaction notes

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