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Diazomethane → HCID 59627290、化合物

HRID 1907733
ノート
印刷プレビュー

反応式

HRID 1907733 の反応式
[OH-].[K+].N(N(C)[C:6](N)=O)=O.[N+](=C)=[N-].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][C:15]=1[NH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:30][CH:29]=1)=[O:27]>O.C(OCC)C.C(Cl)Cl>[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][C:15]=1[NH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH3:6])=[O:37])=[CH:30][CH:29]=1)=[O:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 9550Diazomethane2 回HCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 69100936HCID 69100936、化合物

生成物 1

HCID 59627290HCID 59627290、化合物収率 94.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 3283
Diethyl Ether
溶媒
2 回
HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A mixture of 50% potassium hydroxide in H2O (30 mL) and diethyl ether (100 mL), stirred at 0° C., was treated portion wise with solid N-nitroso-N-methyl urea (3.0 g, 29.1 mmol). The reaction mixture was stirred for 30 min then transferred into a separatory funnel, the aqueous layer was discarded and the yellow ethereal phase (diazomethane solution) was cooled to −78° C. in an Erlenmeyer flask. A suspension of the acid 230 (20 mg, 0.055 mmol) in DCM (2 mL) was treated with the diazomethane solution in diethyl ether (3 mL) and the yellow solution was stirred at room temperature for 3 h, concentrated and the residue was purified by flash chromatography (eluent: 2% isopropanol in DCM) to provide title compound 231 (19.7 mg, 94% yield).

後処理

  1. stirringThe reaction mixture was stirred for 30 min
  2. customthen transferred into a separatory funnel
  3. stirringthe yellow solution was stirred at room temperature for 3 h
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (eluent: 2% isopropanol in DCM)

出典と根拠

ORDレコード
ord-af56a2094a584410bfd7763a289d17d4
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08598168B2

反応ノート

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