Cyanogen Bromide → HCID 19872310, compound

HRID 477744Notes

Reaction equation

HRID 477744 reaction equation
[CH2:1]([S:8][C:9]1[N:13]=[CH:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.N#C[Br:27]>O1CCCC1>[CH2:1]([S:8][C:9]1[N:13]=[C:12]([Br:27])[N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 772049HCID 772049, compoundHCID 178418339Butyllithium

Product 1

HCID 19872310HCID 19872310, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

3-Benzylthio-1-phenyl-1,2,4-triazole (5 g) in dry tetrahydrofuran (50 ml) at -70° C. was treated dropwise with n-butyllithium (1.05 equivs). The solution was stirred at -70° C. for 10 minutes and cyanogen bromide (1.98 g) was added rapidly. The mixture was allowed to warm to room temperature and was then quenched with ethanol. The volatile materials were removed in vacuo, and the crude product was chromatographed on silica using dichloromethane to give 4.3 g of the desired product as a yellow oil.

Workup

  1. temperatureto warm to room temperature
  2. customwas then quenched with ethanol
  3. customThe volatile materials were removed in vacuo
  4. customthe crude product was chromatographed on silica

Sources & evidence

ORD record
ord-15bb7797a8c0414aa1ebc044f8bcd0b9
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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