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

HRID 368382
ノート
印刷プレビュー

反応式

HRID 368382 の反応式
[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]
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

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07e213e56cea42cebb574def8e748fdd
出典データセット
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06133319

反応ノート

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