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Triethylamine → N-(2-hydroxy-4-nitrophenyl)-N'-(2,3-methylenedioxyphenyl)urea

HRID 323055
Notes
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Reaction equation

HRID 323055 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[C:4](C(O)=O)[CH:5]=[CH:6][CH:7]=2)[O:2]1.C([N:15]([CH2:18]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][C:39]=1[OH:47]>C1(C)C=CC=CC=1>[OH:47][C:39]1[CH:40]=[C:41]([N+:44]([O-:46])=[O:45])[CH:42]=[CH:43][C:38]=1[NH:37][C:18]([NH:15][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12)=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3048321,3-Dioxaindane-4-carboxylic acidHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 9883432N-(2-hydroxy-4-nitrophenyl)-N'-(2,3-methylenedioxyphenyl)ureaYield 42%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of the 2,3-methylenedioxyphenylcarboxylic acid in toluene, triethylamine (0.27 mL, 1.95 mmol) and diphenylphosphoryl azide (DPPA) (0.32, mL, 1.5 mmol) were added. The reaction mixture was stirred at 60° C. for 2 hours, then 2-amino-5-nitrophenol (250 mg, 1.5 mmol) was added. The reaction mixture was stirred at 100° C. for 18 hours. After the reaction mixture was cooled to room temperature, it was partitioned between 5% citric acid and ethyl acetate. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. Chromatography of the resulting solid on silica gel (hexane:ethyl acetate; 5:1) gave product (200 mg, 42%). EI-MS m/z 318 (M+H)+

Workup

  1. stirringThe reaction mixture was stirred at 100° C. for 18 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customit was partitioned between 5% citric acid and ethyl acetate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef0995265c31454f9a3e3ffc16bdabb9
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211373B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes