Cyanogen Bromide → HCID 22816303, compound

HRID 1680242Notes

Reaction equation

HRID 1680242 reaction equation
[CH3:1][C@@H:2]1[C@@H:15]2[C@:6]34[CH2:18][CH2:17][N:16]([CH3:19])[C@@H:14]2[CH2:13][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([O:20][C@H:5]3[C:4](=[O:21])[CH2:3]1)[C:7]4=2.[C:22]([O-:25])([O-])=O.[K+].[K+].[N:28]#CBr>C(Cl)(Cl)Cl>[C:19]([N:16]1[CH2:17][CH2:18][C@:6]23[C:7]4[C:8]5[O:20][C@H:5]2[C:4](=[O:21])[CH2:3][C@H:2]([CH3:1])[C@H:15]3[C@H:14]1[CH2:13][C:12]=4[CH:11]=[CH:10][C:9]=5[O:25][CH3:22])#[N:28]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 53643045HCID 53643045, compound

Product 1

HCID 22816303HCID 22816303, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of Compound 7A (9.39 g, 30 mmole; prepared in Example 7A) and powdered anhydrous K2CO3 (6.00 g, 47 mmole) in 60 ml of chloroform was added a solution of cyanogen bromide in chloroform (1.2 eq, 1.0 g/20 ml) dropwise. Stirring was continued for 30 min at about 20° C. after which the mixture was refluxed for 2 hr. After cooling the mixture, the insoluble material therein was removed by filtration. The filtrate was evaporated to a syrup which crystallized upon azeotropic distillation with ethanol. The crystals were boiled with 40 ml of ethanol and collected after storage at 5° C. overnight to give 7.93 g (82% yield) of product, mp 237°-241°.

Workup

  1. temperatureafter which the mixture was refluxed for 2 hr
  2. temperatureAfter cooling the mixture
  3. customthe insoluble material therein was removed by filtration
  4. customThe filtrate was evaporated to a syrup which
  5. customcrystallized upon azeotropic distillation with ethanol
  6. customcollected after storage at 5° C. overnight

Sources & evidence

ORD record
ord-438bcb4de0d24676a203d6e56aa56b18
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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