Thiophosgene → Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(isothiocyanato)picolinate

HRID 1653642Notes

Reaction equation

HRID 1653642 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][C:17]2[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[N:18]=2)=[CH:8][CH:7]=1>ClCCl.O>[CH3:24][O:23][C:21]1[CH:20]=[C:19]([O:25][CH3:26])[N:18]=[C:17]([O:16][C:9]2[C:10]([C:12]([O:14][CH3:15])=[O:13])=[N:11][C:6]([N:5]=[C:1]=[S:2])=[CH:7][CH:8]=2)[N:22]=1

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 15239974Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-aminopicolinate

Product 1

HCID 15239980Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(isothiocyanato)picolinateYield 76.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.82 g (7.15 mmol) of thiophosgene was dropwise added at room temperature to a solution of 2 g (6.5 mmol) of methyl 6-amino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate in 70 ml of dichloromethane and 50 ml of water. The mixture was stirred at room temperature for two hours. After completion of the reaction, the dichloromethane layer was separated and washed with water. Then, the organic layer was dried and concentrated. The obtained residue was recrystallized from a mixture of dichloromethane and diisopropyl ether to obtain the desired product as slightly yellow transparent crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe dichloromethane layer was separated
  3. washwashed with water
  4. customThen, the organic layer was dried
  5. concentrationconcentrated
  6. customThe obtained residue was recrystallized from a mixture of dichloromethane and diisopropyl ether

Sources & evidence

ORD record
ord-27245ae7cd454ec5ba5e209648c27a49
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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