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

HRID 368382
Notes
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Reaction equation

HRID 368382 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-07e213e56cea42cebb574def8e748fdd
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06133319

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes