Water → 2-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 1990992ノート

反応式

HRID 1990992 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1.C(N([CH:23]([CH3:25])C)CC)(C)C.C([NH3+])C.[OH2:29].C[N:31]([CH:33]=[O:34])[CH3:32]>O1CCOCC1>[O:29]=[C:32]1[CH2:25][CH2:23][C:33](=[O:34])[N:31]1[O:15][C:14]([C:12]1[N:13]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[S:10][CH:11]=1)=[O:16]

参加物

7

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27439872-(2,3-dichlorophenyl)-1,3-thiazole-4-carboxylic AcidHCID 3427831Ethanaminium

生成物 1

HCID 589249272-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester収率 87%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

2-(2,3-Dichloro-phenyl)-thiazole-4-carboxylic acid (4.1 g, 15 mmol) was dissolved in a mixture of 50 mL of DMF and 50 mL of dioxane. To this solution diisopropylethylamine (7.8 mL, 45 mmol) and ethanaminium, N-[(dimethylamino)[(2,5-dioxo-1-pyrrolidinyl)oxy]methylene]-N-methyl-, tetrafluoroborate(1-) (TSTU, Aldrich Inc.; 6.8 g, 22.5 mmol) was added. The reaction mixture was stirred at room temperature for 3 h after which 150 mL water was added and the organic layer was separated. The organic layer was extracted with 50 mL water twice, dried and concentrated. The crude mixture was washed with 100 mL isopropanol, to give 2-(2,3-dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (4.8 g, 87% yield) and used without further purification.

後処理

  1. additionwas added
  2. customthe organic layer was separated
  3. extractionThe organic layer was extracted with 50 mL water twice
  4. customdried
  5. concentrationconcentrated
  6. washThe crude mixture was washed with 100 mL isopropanol

出典と根拠

ORDレコード
ord-5b1a48f56d684c1f969be01d81dd89c9
出典データセット
uspto-grants-2010_01
特許番号
US07645773B2

反応ノート

読み込み中…