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

HRID 1199142ノート

反応式

HRID 1199142 の反応式
[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]([O:26]CC)=O)=[S: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:26])[N:19]4[CH2:20][CH2:21][CH2:22][CH2:23][N:18]4[C:16]3=[S:17])[C:2]([F:1])=[CH:3][C:4]=2[S:8][C:7]1=[O:9])[CH:11]=[CH2:12]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 14306486Ethyl 2-[6-fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-ylaminothiocarbonyl]hexahydropyridazine-1-carboxylate

生成物 1

HCID 140498762-[3-(2-propenyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-hexahydro-3-thioxo-1H-[1,2,4]triazolo-[1,2-a]pyridazin-1-one収率 13.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Ethyl 2-[6-fluoro-3-(2-propenyl)-2(3H)-benzothiazolon-5-ylaminothiocarbonyl]hexahydropyridazine-1-carboxylate (2.61 g) was added to a methanolic solution (2.97 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 toluene (1:9) as an eluent to give 2-[3-(2-propenyl)-6-fluoro-2(3H)-benzothiazolon-5-yl]-hexahydro-3-thioxo-1H-[1,2,4]triazolo-[1,2-a]pyridazin-1-one (0.31 g). m.p., 179°-181° C.

後処理

  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 toluene (1:9) as an eluent

出典と根拠

ORDレコード
ord-1ff2575b2d2345429a0de1ce3b226d49
出典データセット
uspto-grants-1990_02
特許番号
US04898948

反応ノート

読み込み中…