Stannous chloride dihydrate → HCID 68277387, compound

HRID 334403Notes

Reaction equation

HRID 334403 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[C:7]([C:22]#[N:23])=[N:8][C:9]([S:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[CH:10][CH:11]=1.O.O.Cl[Sn]Cl>O.Cl>[F:21][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[CH:17]=1)[CH2:13][S:12][C:9]1[N:8]=[C:7]2[C:22]([NH2:1])=[N:23][NH:5][C:6]2=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 23668193Sodium NitriteHCID 68276383HCID 68276383, compound

Product 1

HCID 68277387HCID 68277387, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution cooled to 0° C. of NaNO2 in 3 ml of water is added drop by drop to a solution at 0° C. of 3-amino-6-(3,5-difluorobenzylthio)picolinonitrile (1.587 mmol, 0.44 g) in 15 ml of 6 N HCl solution. After 15 minutes, a solution cooled to 0° C. of SnCl2.2H2O diluted in 4 ml of 12 N HCl is added drop by drop. The reaction medium is then stirred at 25° C. for 1 hour. The solution is extracted with ethyl acetate and then washed using saturated NaHCO3 solution and then saturated NaCl solution. The organic phase is collected, dried on magnesium sulfate and then concentrated under reduced pressure. The residue is purified by silica gel chromatography (AcOEt/heptane) to yield, after concentration of the organic phases, 0.07 g (15%) of black crystals.

Workup

  1. additionis added drop by drop
  2. extractionThe solution is extracted with ethyl acetate
  3. washwashed
  4. customThe organic phase is collected
  5. customdried on magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography (AcOEt/heptane)
  8. customto yield

Sources & evidence

ORD record
ord-6d3d3943576c4fe996b6974c23431a2c
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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