2,6-Dichlorobenzoic acid → 2-(2,6-Dichlorophenylcarbonyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743421

反応式

HRID 743421 の反応式
[Tl].[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:4]=1[C:5]([OH:7])=[O:6].Cl[CH2:14][N:15]1[C:19](=[O:20])[CH:18]([CH2:21][CH2:22][CH3:23])[NH:17][S:16]1(=[O:25])=[O:24]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:4]=1[C:5]([O:7][CH2:14][N:15]1[C:19](=[O:20])[CH:18]([CH2:21][CH2:22][CH3:23])[NH:17][S:16]1(=[O:24])=[O:25])=[O:6]

参加物

6

反応物 3

HCID 57582,6-Dichlorobenzoic acidHCID 5359464ThalliumHCID 194244252-Chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

生成物 1

HCID 158380692-(2,6-Dichlorophenylcarbonyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide収率 29%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

実験手順

The thallium salt of 2,6-dichlorobenzoic acid (0.96 g; 2.43 mmol, prepared from 0.46 g of 2,6-dichlorobenzoic acid and 0.605 g of TlOC2H5 in ethanol ) was added to a solution of 2-chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g; 2.21 mmol) in DMF (10 ml) containing tetrabutylammonium bromide (70 mg; 0.22 mmol). The mixture was allowed to react at 50° C. for 15 hours and at 100° C. for an additional hour, and then cooled. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (25%-30% ethyl acetate in hexane) to afford 0.24 g (29%) of 2-(2,6-dichlorophenylcarbonyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2,6-Cl2 -phenyl; R1 =H; R2 =propyl; R3 =H) as a solid, m.p.95°-97° C.

後処理

  1. customto react at 50° C. for 15 hours and at 100° C. for an additional hour
  2. temperaturecooled
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (25%-30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-43730bc26c034a619390e78ce92ec417
出典データセット
uspto-grants-1996_09
特許番号
US05556909

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