Triethylamine → O-(1-isopropylpyrazol-4-yl) N-(2-cyanoprop-2-ylsulphenyl)-N-methyl-carbamate

HRID 485066Notes

Reaction equation

HRID 485066 reaction equation
[C:1]([C:3]([S:6][N:7]([CH3:11])[C:8](F)=[O:9])([CH3:5])[CH3:4])#[N:2].[OH:12][C:13]1[CH:14]=[N:15][N:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([C:3]([S:6][N:7]([CH3:11])[C:8](=[O:9])[O:12][C:13]1[CH:14]=[N:15][N:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=1)([CH3:5])[CH3:4])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130184111-(Propan-2-yl)-1H-pyrazol-4-olHCID 13340646N-(2-cyanoprop-2-ylsulphenyl)-N-methyl-carbamoyl fluoride

Product 1

HCID 13340647O-(1-isopropylpyrazol-4-yl) N-(2-cyanoprop-2-ylsulphenyl)-N-methyl-carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

12 g (0.075 mole) of N-(2-cyanoprop-2-ylsulphenyl)-N-methyl-carbamoyl fluoride are added dropwise to a mixture of 9.45 g (0.075 mole) of 4-hydroxy-1-isopropylpyrazole, 8.5 g (0.085 mole) of triethylamine and 100 ml of toluene at 25° C. When the addition has ended, the mixture is stirred at room temperature for 18 hours. For working up, the reaction mixture is washed twice with water, dried over sodium sulphate and freed from the solvent in vacuo. 18 g (85% of theory) of O-(1-isopropylpyrazol-4-yl) N-(2-cyanoprop-2-ylsulphenyl)-N-methyl-carbamate are obtained in the form of a yellow oil of refractive index nD21 1.5070.

Workup

  1. additionWhen the addition
  2. washthe reaction mixture is washed twice with water
  3. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-adac67ad5f4b4ce38650cf05607271b5
Source dataset
uspto-grants-1985_08
Patent number
US04535091

Reaction notes

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