Pyridine → HCID 135555957, compound

HRID 968211Notes

Reaction equation

HRID 968211 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)[NH:5][C:4](=[O:16])[CH:3]=1.N1C=CC=CC=1.[S-:23][C:24]#[N:25].[K+].BrBr>CN(C=O)C>[NH2:25][C:24]1[S:23][C:3]2[C:4](=[O:16])[NH:5][C:6]([S:8][CH2:9][C:10]3[N:11]=[C:12]([CH3:15])[S:13][CH:14]=3)=[N:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 135555956HCID 135555956, compound

Product 1

HCID 135555957HCID 135555957, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from step (a) (24.3 g) was stirred in dry DMF (400 ml) with pyridine (13.1 ml) and potassium thiocyanate (37.1 g) at 0C. Bromine (4.5 ml) was added over 1 hr and the mixture kept at 0C for a further 2 hrs. The mixture was poured onto water to give a solution which was then evaporated to low volume. Water was added to give a precipitate which was collected. The solid was dissolved in dilute hydrochloric acid and reprecipitated by the addition of sodium bicarbonate solution. The solid was collected, washed with water and dried to afford the sub-title compound (8.7 g)

Workup

  1. additionThe mixture was poured onto water
  2. customto give a solution which
  3. customwas then evaporated to low volume
  4. additionWater was added
  5. customto give a precipitate which
  6. customwas collected
  7. dissolutionThe solid was dissolved in dilute hydrochloric acid
  8. customreprecipitated by the addition of sodium bicarbonate solution
  9. customThe solid was collected
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-aeb1f4c940494eac9f6715d01ff5352a
Source dataset
uspto-grants-2005_10
Patent number
US06958343B2

Reaction notes

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