Cyanogen Bromide → HCID 13324092, compound

HRID 637715Notes

Reaction equation

HRID 637715 reaction equation
[N:1]#[C:2]Br.C(=O)([O-])[O-].[K+].[K+].C[CH:11]1[CH2:16][CH:15]([C:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19][N:18]=2)[CH2:14][CH2:13][NH:12]1>C(Cl)(Cl)Cl>[C:2]([N:12]1[CH2:11][CH2:16][CH:15]([C:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19][N:18]=2)[CH2:14][CH2:13]1)#[N:1]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 18365329HCID 18365329, compound

Product 1

HCID 13324092HCID 13324092, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 5.9 g of cyanogen bromide, 8.6 g of potassium carbonate, and 80 ml of chloroform was added, dropwise, 11.0 g of 3-(2-methyl-4-piperidinyl)-1,2-benzisothiazole, in 30 ml of chloroform. The mixture was stirred under reflux for 4 hrs, cooled, filtered and the filtrate was concentrated in vacuo to a solid. The solid was triturated with hexane and recrystallized from methanol-water (twice) to yield 4.5 g (36%) of product, mp 118°-120°.

Workup

  1. additionwas added
  2. temperatureunder reflux for 4 hrs
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo to a solid
  6. customThe solid was triturated with hexane
  7. customrecrystallized from methanol-water (twice)

Sources & evidence

ORD record
ord-b733ac421d1f4a93b6e009f490d5fd32
Source dataset
uspto-grants-1985_12
Patent number
US04558056

Reaction notes

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