ethyl 2-(4-chloro-2-fluoro-5-(-methylethoxy)phenylaminothioxometyl)-3,4,5,6-tetrahydro1(2H)pyridazinecarboxylate → N-(4-chloro-2-fluoro-5-isopropoxyphenyl)tetrahydro-1(2H)-pyridazinecarbothioamide

HRID 1262630Notes

Reaction equation

HRID 1262630 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:13](=[S:25])[N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]2C(OCC)=O)=[C:4]([F:26])[CH:3]=1>[OH-].[K+]>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][C:5]([NH:12][C:13](=[S:25])[N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)=[C:4]([F:26])[CH:3]=1

Participants

3

Reactant 1

HCID 15590227ethyl 2-(4-chloro-2-fluoro-5-(-methylethoxy)phenylaminothioxometyl)-3,4,5,6-tetrahydro1(2H)pyridazinecarboxylate

Product 1

HCID 15590083N-(4-chloro-2-fluoro-5-isopropoxyphenyl)tetrahydro-1(2H)-pyridazinecarbothioamideYield 45.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of ethyl 2-(4-chloro-2-fluoro-5-(-methylethoxy)phenylaminothioxometyl)-3,4,5,6-tetrahydro1(2H)pyridazinecarboxylate (0.8 g) in a 5% ethanolic potassium hydroxide solution (10 ml) was heated under reflux for 3 hours. After being allowed to cool to room temperature, ethanol was removed under reduced pressure. The residue was dissolved in ether, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 0.3 g of 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenylaminothioxomethyl)-3,4,5,6-tetrahydro-(1H,2H)-pyridazine. M.P., 113°-114.5° C. δ (ppm): 1.35 (6H, d), 1.7 (4H, m), 2.95 (2H, m), 3.45 (1H, t), 4.2 (2H, m), 4.4 (1H, m), 6.95 (1H, d), 8.25 (1H, d), 9.85 (1H, m).

Workup

  1. temperatureunder reflux for 3 hours
  2. customethanol was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-87069829c2894b02ac0e5833a26dbaf7
Source dataset
uspto-grants-1984_06
Patent number
US04452981

Reaction notes

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