Cyanogen Bromide → HCID 13324092, compound

HRID 370709Notes

Reaction equation

HRID 370709 reaction equation
[N:1]#CBr.C([O-])([O-])=O.[K+].[K+].[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19][N:18]=2)[CH2:13][CH2:12]1>C(Cl)(Cl)Cl>[C:10]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19][N:18]=2)[CH2:13][CH2:12]1)#[N:1]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 13324091HCID 13324091, compound

Product 1

HCID 13324092HCID 13324092, compoundYield 108.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of CNBr (5.9 g, 0.056 mole), K2CO3 (8.6 g) and CHCl3 (80 ml) was added dropwise 3-(1-methyl-4-piperidinyl)-1,2-benzisothiazole (11.0 g, 0.051 mole) in CHCl3 (30 ml). The mixture was stirred and refluxed for 4 hours and thereafter cooled and filtered. The filtrate was concentrated in vacuo to a solid. The solid was triturated with hexane and collected to yield 13.5 g of the desired compound. Recrystallization from MeOH--H2O (twice) yielded 4.5 g (36%) of the benzisothiazole, m.p. 118°-120°.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to a solid
  5. customThe solid was triturated with hexane
  6. customcollected

Sources & evidence

ORD record
ord-79db1c5b52ff4d72aec99cb44e7ee2a7
Source dataset
uspto-grants-1985_07
Patent number
US04528292

Reaction notes

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