Pyridine → HCID 14213641, compound

HRID 1940017Notes

Reaction equation

HRID 1940017 reaction equation
[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([CH2:9]O)=[C:6]([Cl:8])[N:7]=1.N1C=CC=CC=1.S(Cl)([Cl:21])=O.[K+].[Br-]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([CH2:9][Cl:21])=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 253877Potassium BromideHCID 21465301HCID 21465301, compound

Product 1

HCID 14213641HCID 14213641, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 2 (3.7 g, 0.02 mole) was suspended in 40 ml of chloroform. To this mixture, 1.8 ml of pyridine and 3.0 ml of thionyl chloride were added slowly while stirring. At the end of this addition, the mixture was stirred for four additional hours at room temperature. The solvent was then removed, and the residue was triturated with 100 ml of cold water. After filtration and washing with cold water, the product (4) was dried in air, yielding 4.0 g (91%) of light yellow solid. The melting point of this solid ranged from 173°-174° C. The IR spectrum (KBr) showed absorptions corresponding to --NH2 at 3201 and 3365.8 cm-1, --C≡N at 2237.6, and --C=N-- at 1648.7 cm-1. The nmr spectrum (DMSO-d6) revealed signals at 7.76 δ (2H, s,NH2) and 4.60 (2H,s,CH2C1).

Workup

  1. additionAt the end of this addition
  2. stirringthe mixture was stirred for four additional hours at room temperature
  3. customThe solvent was then removed
  4. customthe residue was triturated with 100 ml of cold water
  5. filtrationAfter filtration
  6. washwashing with cold water
  7. dry with materialthe product (4) was dried in air
  8. customyielding 4.0 g (91%) of light yellow solid
  9. customranged from 173°-174° C

Sources & evidence

ORD record
ord-1f0faf81f0e74136b273578ab453dc7b
Source dataset
uspto-grants-1997_12
Patent number
US05698556

Reaction notes

Loading…