Water → 2-Chloro-6-(4-isothiocyanatophenoxy)pyridine

HRID 1415083Notes

Reaction equation

HRID 1415083 reaction equation
[C:1](Cl)(Cl)=[S:2].O.C(COC)OC.[Cl:12][C:13]1[N:18]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>CCCCCC>[Cl:12][C:13]1[N:18]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]=[C:1]=[S:2])=[CH:22][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80711,2-Dimethoxyethane2×HCID 10040Thiophosgene2×HCID 13980869Benzenamine, 4-[(6-chloro-2-pyridinyl)oxy]-

Product 1

HCID 213914182-Chloro-6-(4-isothiocyanatophenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Thiophosgene (10.5 grams; 0.091 mole) was added to an agitated solution of water (170 ml.) and dimethoxyethane (25 ml.) 4-((6-Chloro-2-pyridinyl)oxy)benzenamine (20 grams; 0.0906 mole) was added in small portions (the dimethoxyethane aids in suspending the amine in the aqueous thiosphosgene solution) to the stirred thiophosgene solution over a 20 minute period. The reactive temperature during the addition was 25°-30° C. Following the addition of the amine reactant, the reaction mixture was filtered to recover the product precipitate which formed during the reaction. The precipitate was then dissolved in boiling hexane and the resulting solution dried and cooled to give the desired 4-((6-chloro-2-pyridinyl)oxy)phenyl isothiocyanate product as a light yellow crystalline solid having a melting point of 59°-62° C. The product was found to have carbon, hydrogen, nitrogen, chlorine and sulfur contents of 55.5, 2.3, 10.9, 13.36 and 12.34 percent, respectively, as compared with the theoretical contents of 54.82, 2.69, 10.66, 13.5 and 12.2 percent, respectively, calculated for the named structure.

Workup

  1. customover a 20 minute
  2. additionThe reactive temperature during the addition
  3. customwas 25°-30° C
  4. filtrationthe reaction mixture was filtered
  5. customto recover the product precipitate which
  6. customformed during the reaction
  7. dissolutionThe precipitate was then dissolved
  8. customthe resulting solution dried
  9. temperaturecooled

Sources & evidence

ORD record
ord-c95600b2b1a24504b20ae0e0825d20b0
Source dataset
uspto-grants-1977_01
Patent number
US04003733

Reaction notes

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