Sodium hydride → 3-(2,3-Dichlorophenylthiomethyl)-5-methyl-1,2,4-oxadiazole

HRID 22296

反応式

HRID 22296 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[SH:9].[H-].[Na+].Cl[CH2:13][C:14]1[N:18]=[C:17]([CH3:19])[O:16][N:15]=1>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9][CH2:13][C:14]1[N:18]=[C:17]([CH3:19])[O:16][N:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1402022,3-DichlorobenzenethiolHCID 3021573-(Chloromethyl)-5-methyl-1,2,4-oxadiazole

生成物 1

HCID 199286583-(2,3-Dichlorophenylthiomethyl)-5-methyl-1,2,4-oxadiazole収率 40.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

7.0 g (39.1 mmol) of 2,3-dichloro-thiophenol are introduced into 50 ml of absolute tetrahydrofuran, the mixture is treated with 1.2 g (0.039 mmol) of 80% sodium hydride dispersion in portions and stirred for 2 hours at reflux temperature. The mixture is subsequently treated with 4.5 g (33.9 mmol) of 3-chloromethyl-5-methyl-1,2,4-oxadiazole at room temperature and stirred until the reaction is complete (approximately 10 to 15 hours). The sodium chloride which has precipitated is subsequently separated off and the entire batch is concentrated in vacuo. The crude product which remains can be chromatographed over a silica gel column (silica gel 60-Merck, particle size: 0.040 to 0.063 mm) using toluene as the eluent. 3.8 g (36.5% of theory) of 3-(2,3-dichlorophenylthiomethyl)-5-methyl-1,2,4-oxadiazole are obtained.

後処理

  1. temperatureat reflux temperature
  2. stirringstirred until the reaction
  3. custom(approximately 10 to 15 hours)
  4. customThe sodium chloride which has precipitated
  5. customis subsequently separated off
  6. concentrationthe entire batch is concentrated in vacuo
  7. customThe crude product which remains can be chromatographed over a silica gel column (silica gel 60-Merck, particle size: 0.040 to 0.063 mm)

出典と根拠

ORDレコード
ord-bfc60d7b03054bb0bd5938345113d8c0
出典データセット
uspto-grants-1995_06
特許番号
US05428047

関連ノート

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