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Diazomethane → HCID 59627290, 화합물

HRID 1907733
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HRID 1907733 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 9550Diazomethane2회HCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 69100936HCID 69100936, 화합물

생성물 1

HCID 59627290HCID 59627290, 화합물수율 94.1%

시약·촉매·용매 3

HCID 962Water용매
HCID 3283
Diethyl Ether
용매
2회
HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-af56a2094a584410bfd7763a289d17d4
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598168B2

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