1,2-Diazinane → 1-[2-Chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl ester

HRID 1646468Notes

Reaction equation

HRID 1646468 reaction equation
[CH3:1][O:2][C:3]([C:5]1([S:8][C:9]2[CH:14]=[C:13]([N:15]=[C:16]=[S:17])[C:12]([F:18])=[CH:11][C:10]=2[Cl:19])[CH2:7][CH2:6]1)=[O:4].[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1>C(O)C>[CH3:1][O:2][C:3]([C:5]1([S:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]3)=[S:17])[C:12]([F:18])=[CH:11][C:10]=2[Cl:19])[CH2:6][CH2:7]1)=[O:4]

Participants

4

Reactant 2

HCID 1363341,2-DiazinaneHCID 545373801-(2-Chloro-4-fluoro-5-isothiocyanato-phenylthio)-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 867464931-[2-Chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl esterYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

While stirring at room temperature, a solution of 6.3 g of 1-(2-chloro-4-fluoro-5-isothiocyanato-phenylthio)-cyclopropanecarboxylic acid methyl ester in 30 ml of ethanol is added dropwise to a solution of 2.2 g of hexahydropyridazine in 30 ml of ethanol. After stirring for 30 minutes at room temperature, the reaction mixture is concentrated by evaporation in vacuo, yielding 7.9 g of 1-[2-chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl ester having a melting point of from +156° to +157° C.

Workup

  1. stirringAfter stirring for 30 minutes at room temperature
  2. concentrationthe reaction mixture is concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-bf5d1cf10c2544afa338c3e4b6e08b54
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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