Hydrochloric Acid → 2-Chloro-5-(phenylthio)pyridine

HRID 372735Notes

Reaction equation

HRID 372735 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1.[ClH:15].N([O-])=O.[Na+].[OH-].[Na+]>O>[Cl:15][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 124108405-(Phenylsulfanyl)pyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 111953972-Chloro-5-(phenylthio)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

Alternatively, 2-amino-5-(phenylthio) pyridine (30 g., 0.15 moles) is added portionwise to 30 ml. of concentrated hydrochloric acid at 0°. The resultant suspension is cooled to -15° C and 20.7 g. of sodium nitrite in 40 ml. of water is added dropwise while keeping the temperature at -15° to -10° C. After stirring for an additional hour at -5° C, an aqueous 30% sodium hydroxide solution is slowly added to pH7 while not allowing the temperature to exceed 0° C. The resultant mixture is extracted with methylene chloride and the combined extracts are washed with water, dried and evaporated in vacuo to yield 2-chloro-5-(phenylthio) pyridine.

Workup

  1. customat 0°
  2. customat -15° to -10° C
  3. customto exceed 0° C
  4. extractionThe resultant mixture is extracted with methylene chloride
  5. washthe combined extracts are washed with water
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a619d54da48c4b36b13dcde7bfed0882
Source dataset
uspto-grants-1978_05
Patent number
US04092321

Reaction notes

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