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2-Methoxyethylamine → N-(2-Hydroxy-4-nitrophenyl)-N'-(2-methoxyethyl)urea

HRID 368381
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HRID 368381 반응식
[Si]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH2:11])(C(C)(C)C)(C)C.Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH3:38][O:39][CH2:40][CH2:41][NH2:42]>C1(C)C=CC=CC=1>[OH:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH:11][C:20]([NH:42][CH2:41][CH2:40][O:39][CH3:38])=[O:22]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 154857102-[(Tert-butyldimethylsilyl)oxy]-4-nitroaniline

생성물 1

HCID 23288457N-(2-Hydroxy-4-nitrophenyl)-N'-(2-methoxyethyl)urea수율 124.1%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
80 °C

실험 절차

To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (200 mg, 0.75 mmol) in toluene (5 mL), triphosgene (84 mg, 0.3 mmol) and triethylamine (0.13 mL, 0.9 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-methoxyethylamine (56.3 mg, 0.75 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (95 mg, 50%). EI-MS m/z 256.2 (M+). mp: 190.0-190.7° C.

후처리

  1. temperatureThen it was cooled to room temperature
  2. customall solvent was evaporated
  3. dissolutionThe residue was dissolved in DMF (1 mL)
  4. stirringThe reaction mixture was stirred at 80° C. for 16 hours

출처 및 근거

ORD 기록
ord-e32a29067b2640b49c7c561dd85cfe3c
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06133319

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