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

HRID 22296

반응식

HRID 22296 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bfc60d7b03054bb0bd5938345113d8c0
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428047

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