Chlorine → 4-Methoxy-3-(6-methoxy-3-pyridylmethyl)phenylthiocyanate

HRID 1165621Notes

Reaction equation

HRID 1165621 reaction equation
ClCl.[Pb]([S:7][C:8]#[N:9])SC#N.[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])=[CH:14][CH:13]=1>C(O)(=O)C>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][C:23]([S:7][C:8]#[N:9])=[CH:24][C:19]=1[CH2:18][C:15]1[CH:16]=[N:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 24526ChlorineHCID 516874BleirhodanidHCID 146734412-(6-Methoxy-3-pyridylmethyl)-anisole

Product 1

HCID 146735234-Methoxy-3-(6-methoxy-3-pyridylmethyl)phenylthiocyanateYield 123.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To dry acetic acid (250 ml, dried by refluxing with 5% acetic anhydride for 4.5 hours) was added dry chlorine (16.00 g). Lead thiocyanate (36.48 g) was added in portions with rapid stirring then after 40 minutes 2-(6-methoxy-3-pyridylmethyl)-anisole (45.85 g) in dry acetic acid (175 ml) was added slowly from a dropping funnel. The mixture was stirred at room temperature for 20 hours, filtered, poured into water (approximately 2 litres) and extracted with chloroform. The combined chloroform extracts were washed with water, 2N sodium hydroxide, water, then dried with anhydrous magnesium sulphate and evaporated to dryness to give an orange gum which was crystallised from chloroform/petroleum spirit (60°-80°) to give 4-methoxy-3-(6-methoxy-3-pyridylmethyl)phenylthiocyanate as a yellow solid (39.89 g, 55%), m.p. 56°-58°.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 hours
  2. filtrationfiltered
  3. additionpoured into water (approximately 2 litres)
  4. extractionextracted with chloroform
  5. washThe combined chloroform extracts were washed with water, 2N sodium hydroxide, water
  6. dry with materialdried with anhydrous magnesium sulphate
  7. customevaporated to dryness
  8. customto give an orange gum which
  9. customwas crystallised from chloroform/petroleum spirit (60°-80°)

Sources & evidence

ORD record
ord-3f4bdb7a32994b109ebfc4f25aac81cc
Source dataset
uspto-grants-1990_03
Patent number
US04910305

Reaction notes

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