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

HRID 1731469Notes

Reaction equation

HRID 1731469 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]=[C:13]=[S:14])=[C:4]([F:15])[CH:3]=1.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][NH:22]1)=[O:20])[CH3:17].O>C(N(CC)CC)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][C:5]([NH:12][C:13](=[S:14])[N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][N:21]2[C:19]([O:18][CH2:16][CH3:17])=[O:20])=[C:4]([F:15])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 30143771(2H)-Pyridazinecarboxylic acid, tetrahydro-, ethyl esterHCID 136079331-Chloro-5-fluoro-4-isothiocyanato-2-[(propan-2-yl)oxy]benzene

Product 1

HCID 15590227ethyl 2-(4-chloro-2-fluoro-5-(-methylethoxy)phenylaminothioxometyl)-3,4,5,6-tetrahydro1(2H)pyridazinecarboxylateYield 43.5%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent

Procedure

4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl isothiocyanate (2.8 g) was added to a solution of 2-ethoxycarbonyl-3,4,5,6-tetrahydro-(1H, 2H)-pyridazine (1.8 g) and several drops of triethylamine in toluene (5 ml), and the resultant mixture was stirred at 25° C. overnight. Water was added to the mixture, which was then extracted with toluene. The toluene layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography to give 2 g of ethyl 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenylaminothioxomethyl)-3,4,5,6-tetrahydro-1(2H)pyridazine carboxylate. nD27.5 1.5534. NMR δ (ppm): 1.3 (3H, t), 1.4 (6H, d), 1.8 (4H, m), 4.35 (2H, q), 7.1 (1H, d), 8.0 (1H, d), 8.45 (1H, m, ##STR12##

Workup

  1. extractionwas then extracted with toluene
  2. washThe toluene layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d16b50b34314f6692eb34a5e34c211c
Source dataset
uspto-grants-1986_11
Patent number
US04622063

Reaction notes

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