Pyridine → HCID 135555957, compound

HRID 1097349Notes

Reaction equation

HRID 1097349 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.[S-:17][C:18]#[N:19].[K+].N1C=CC=CC=1.BrBr>CN(C=O)C.O>[NH2:19][C:18]1[S:17][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

7

Reactant 4

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

Product 1

HCID 135555957HCID 135555957, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from example 20 step a) (24.3 g) and potassium thiocyanate (37.1 g) was stirred in dry DMF (400 ml) with pyridine (13.1 ml) at 0° C. Bromine (4.5 ml) was added over 1 hr. After stirring 2 hrs the mixture was poured into water. The resulting solution was concentrated to low volume then water added. The resulting solid was collected, taken up in 2M hydrochloric acid and precipitated by the addition of saturated sodium bicarbonate solution. The solid was collected, washed with water and dried to give the sub-title compound, (8.7 g).

Workup

  1. concentrationThe resulting solution was concentrated to low volume
  2. additionwater added
  3. customThe resulting solid was collected
  4. customprecipitated by the addition of saturated sodium bicarbonate solution
  5. customThe solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-5f69b871856a4aae8cdcae846b8761bc
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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