Sodium hydride → 1-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazole

HRID 892259ノート

反応式

HRID 892259 の反応式
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[C:7]([CH3:13])[CH:6]=1)[CH:2]=[CH2:3].[N:14]1([CH2:19][CH2:20]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:18]=[CH:17][N:16]=[N:15]1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][CH2:20][CH2:19][N:14]2[CH:18]=[CH:17][N:16]=[N:15]2)=[C:7]([CH3:13])[CH:6]=1)[CH:2]=[CH2:3]

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 22242072(4-Allyloxy-2-methyl-phenyl)-methanethiolHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

生成物 1

HCID 222420831-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazole収率 94.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a mixture of 1.98 g (10.2 mmol) (4-allyloxy-2-methyl-phenyl)-methanethiol and 2.72 g (10.2 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester in 25 ml N,N-dimethylformamide was added under argon at −50° C. 515 mg (20.4 mmol) sodium hydride. The mixture was allowed to warm up to room temperature and was stirred under argon for 12 hours. 80% of the DMF was stilled off in vacuo, ethyl acetate and water given to the mixture. The aqueous phase was reextracted with ethyl acetate and the combined organic extracts dried and evaporated to yield 2.8 g of 1-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazole as brown oil. The raw material (73% purity) was used without further purification.

後処理

  1. additionwas added under argon at −50° C
  2. customthe combined organic extracts dried
  3. customevaporated

出典と根拠

ORDレコード
ord-cd96bc8283bc4b05a80a37544652ec7f
出典データセット
uspto-grants-2006_02
特許番号
US07005526B2

反応ノート

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