Cyanogen Bromide → HCID 86737294, compound

HRID 904221Notes

Reaction equation

HRID 904221 reaction equation
Cl.[CH3:2][C@H:3]1[C@H:16]([CH2:17][CH3:18])[C@@H:15]2[C@:6]3([CH2:21][CH2:20][N:19]([CH3:22])[C@@H:14]2[CH2:13][C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]3=2)[CH2:5][C:4]1=[O:23].[C:24](=[O:27])([O-])[O-].[K+].[K+].[N:30]#CBr>C(Cl)(Cl)Cl>[C:22]([N:19]1[CH2:20][CH2:21][C@@:6]23[C:7]4[CH:8]=[C:9]([O:27][CH3:24])[CH:10]=[CH:11][C:12]=4[CH2:13][C@@H:14]1[C@@H:15]2[C@@H:16]([CH2:17][CH3:18])[C@H:3]([CH3:2])[C:4](=[O:23])[CH2:5]3)#[N:30]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 70552154HCID 70552154, compound

Product 1

HCID 86737294HCID 86737294, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 9 (11.30 g, 34.5 mmol) and potassium carbonate (7.15 g, 51.8 mmol) in chloroform (75 ml) was added dropwise cyanogen bromide (4.45 g, 42.0 mmol) in chloroform. The reaction mixture was refluxed for 2 hours and processed as above to give 10.6 g (86%) of 12 as a foam after azeotroping with EtOH. The foam was used without further characterization in the hydrolysis reaction.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours

Sources & evidence

ORD record
ord-496064c9cc4141c984ddc384a5e136b2
Source dataset
uspto-grants-1980_10
Patent number
US04230712

Reaction notes

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