Cyanogen Bromide → HCID 18699937, compound

HRID 2288608Notes

Reaction equation

HRID 2288608 reaction equation
[N:1]#[C:2]Br.[N:4]1([CH2:11][C:12]2[S:13][C:14]([C:17]([NH:19][NH2:20])=[O:18])=[CH:15][CH:16]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>C(O)C>[NH2:1][C:2]1[O:18][C:17]([C:14]2[S:13][C:12]([CH2:11][N:4]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)=[CH:16][CH:15]=2)=[N:19][N:20]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 55213626HCID 55213626, compound

Product 1

HCID 18699937HCID 18699937, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g (23.57 mmol) of cyanogen bromide was added to 250 ml of ethanol solution containing 5.43 g (21.43 mmol) of 2-(hexahydro-1H-azepin-1-yl)methylthiophene-5-carboxylic acid hydrazide, and the mixture was stirred at room temperature for 2 hours and then at 50° C. for 7 hours. The reaction solution was concentrated under a reduced pressure, saturated sodium bicarbonate aqueous solution and chloroform were added to the resulting residue. Then, the resulting organic layer was separated, washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was recrystallized from ethyl acetate to give 2.43 g of the title compound.

Workup

  1. waitat 50° C. for 7 hours
  2. concentrationThe reaction solution was concentrated under a reduced pressure, saturated sodium bicarbonate aqueous solution and chloroform
  3. additionwere added to the resulting residue
  4. customThen, the resulting organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b92c754fe7404644b17285bea76c60fc
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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