Sodium Hydroxide → [(4-Chloro-1H-pyrazol-1-yl)oxy]methyl thiocyanate

HRID 34952

Reaction equation

HRID 34952 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][N:7]([OH:9])[CH:8]=1.Cl[CH2:11][S:12][C:13]#[N:14].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[N:6][N:7]([O:9][CH2:11][S:12][C:13]#[N:14])[CH:8]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 76755Thiocyanic acid, chloromethyl esterHCID 2723671Tetrabutylammonium HydroxideHCID 133912524-Chloro-1H-pyrazol-1-ol

Product 1

HCID 14011041[(4-Chloro-1H-pyrazol-1-yl)oxy]methyl thiocyanateYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 ml of a 5% strength aqueous sodium hydroxide solution were added to 5 g (42 mMol) of 4-chloro-1-hydroxypyrazole, 13.5 g (126 mMol) of chloromethyl thiocyanate and 50 ml of methylene chloride. After the addition of 1 g (4 mMol) of tetra-n-butylammonium hydroxide, the mixture was stirred at room temperature for 24 hours. Thereafter, the organic phase was separated off, dried and evaporated down. Distillation of the residue under reduced pressure (airbath at 140° C./3 mbar) gave 5.7 g (71% of theory) of 4-chloro-1-[(thiocyanato)-methoxy]-pyrazole (compound No. 1), which was recrystallized from ether/petroleum ether (mp. 60° C.).

Workup

  1. customThereafter, the organic phase was separated off
  2. customdried
  3. customevaporated down
  4. distillationDistillation of the residue under reduced pressure (airbath at 140° C./3 mbar)

Sources & evidence

ORD record
ord-e1f2e11ee6ab46f19657e1637b95bd26
Source dataset
uspto-grants-1988_08
Patent number
US04764527

Linked notes

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