Triethylamine → N-(2-Hydroxy-4-nitrophenyl)-N'-(2-benzyloxypropyl)urea

HRID 368382

반응식

HRID 368382 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.[CH2:38]([O:45][CH:46]([CH3:49])[CH2:47][NH2:48])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>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:48][CH2:47][CH:46]([O:45][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:49])=[O:22]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2960152-(Benzyloxy)propan-1-amineHCID 154857102-[(Tert-butyldimethylsilyl)oxy]-4-nitroaniline

생성물 1

HCID 15485714N-(2-Hydroxy-4-nitrophenyl)-N'-(2-benzyloxypropyl)urea수율 103%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (300 mg, 1.125 mmol) in toluene (10 mL), triphosgene (126 mg, 0.45 mmol) and triethylamine (0.195 mL, 1.35 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-benzyloxypropylamine (185.6 mg, 1.125 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 (160 mg, 41%). EI-MS m/z 346.4 (M+). mp: 64.6-65.2° 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-07e213e56cea42cebb574def8e748fdd
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133319

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