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 1731470Notes

Reaction equation

HRID 1731470 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-(1-methylethoxy)phenylaminothioxomethyl)-3,4,5,6-tetrahydro-1(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. NMR 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-2d911a6de5ef4ae4adc1e04bb87a4f16
Source dataset
uspto-grants-1986_11
Patent number
US04622063

Reaction notes

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