Sodium Methoxide → 2-[3-(2-propenyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-hexahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione

HRID 2232004Notes

Reaction equation

HRID 2232004 reaction equation
[F:1][C:2]1[C:14]([NH:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24](OCC)=[O:25])=[O:17])=[CH:13][C:5]2[N:6]([CH2:10][CH:11]=[CH2:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.C[O-].[Na+]>O>[CH2:10]([N:6]1[C:5]2[CH:13]=[C:14]([N:15]3[C:24](=[O:25])[N:19]4[CH2:20][CH2:21][CH2:22][CH2:23][N:18]4[C:16]3=[O:17])[C:2]([F:1])=[CH:3][C:4]=2[S:8][C:7]1=[O:9])[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14049866Ethyl 2-[6-fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-ylaminocarbonyl]-hexahydropyridazine-1-carboxylate

Product 1

HCID 140498672-[3-(2-propenyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-hexahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dioneYield 10.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-[6-fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-ylaminocarbonyl]-hexahydropyridazine-1-carboxylate (1.55 g) was added to a methanolic solution (2.05 g) of 10% sodium methoxide, and the resultant mixture was heated under reflux for 1.5 hours and allowed to cool. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried, concentrated and purified by silica gel thin layer chromatography with a mixture of ethyl acetate and hexane (1:1) as an eluent to give 2-[3-(2-propenyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-hexahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione (0.15 g). m.p., 199.5° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. temperatureto cool
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel thin layer chromatography with a mixture of ethyl acetate and hexane (1:1) as an eluent

Sources & evidence

ORD record
ord-2b0ec1dfba69422986d2025c7308c1ea
Source dataset
uspto-grants-1988_11
Patent number
US04786310

Reaction notes

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