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Glycidol → p-(N-2,3-dihydroxypropylamino)benzonitrile

HRID 1029
ノート
印刷プレビュー

反応式

HRID 1029 の反応式
[O-]C1C=CC=CC=1.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][CH:19]([CH2:21][O:22]S(C)(=O)=O)[O:18]C2=O)=[CH:12][CH:11]=1)#[N:9].NC1C=CC(C#N)=CC=1.O1CC1CO>CN(C)C=O>[OH:18][CH:19]([CH2:21][OH:22])[CH2:20][NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]#[N:9])=[CH:11][CH:12]=1
参加物実験手順出典と根拠反応ノート

参加物

6

反応物 4

HCID 11164GlycidolHCID 133964-AminobenzonitrileHCID 119047PhenolateHCID 152815273-p-Cyanophenyl-5-methanesulfonyloxymethyloxazolidin-2-one

生成物 1

HCID 10171309p-(N-2,3-dihydroxypropylamino)benzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1 Equivalent of NaH is added to a solution of 1.7 g of Na p-methoxycarbonylmethylphenoxide (obtainable by converting p-hydroxybenzyl cyanide into the corresponding carboxylic acid, esterifying with methanol to give p-methoxycarbonylmethylphenol and subsequently converting the latter into the phenoxide) in 20 ml of dimethylformamide (DMF), and the mixture is stirred at room temperature for 30 min. After that, 3.0 g of 3-p-cyanophenyl-5-methanesulfonyloxymethyloxazolidin-2-one ("A") (obtainable by reacting p-aminobenzonitrile with 2,3-epoxypropan-1-ol to give p-(N-2,3-dihydroxypropylamino)benzonitrile, reacting the latter with diethyl carbonate in the presence of K tert-butoxide to give 3-p-cyanophenyl-5-hydroxymethyloxazolidin-2-one and subsequently esterifying the latter with methanesulfone chloride), dissolved in 10 ml of DMF, are added and the mixture is once again stirred at room temperature for 15 min. Following removal of the solvent, and the customary working-up, 3-p-cyanophenyl-5-(p-methoxycarbonylmethylphenoxymethyl)oxazolidin-2-one is obtained, M.p. 114°-115°.

出典と根拠

ORDレコード
ord-db32eb67f898496ca933619d4788c566
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05723480

反応ノート

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