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Triethylamine → HCID 9845158, compound

HRID 973448
Notes
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Reaction equation

HRID 973448 reaction equation
[CH2:1]([C:10]1[CH:18]=[CH:17][C:13](C(O)=O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C([N:21]([CH2:24]C)CC)C.[O:26](P(N=[N+]=[N-])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[CH:45]([C:48]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]([CH3:57])[CH3:56])[C:49]=1[NH2:50])([CH3:47])[CH3:46]>C1(C)C=CC=CC=1>[CH2:1]([C:10]1[CH:11]=[CH:12][C:13]([NH:21][C:24]([NH:50][C:49]2[C:48]([CH:45]([CH3:47])[CH3:46])=[CH:54][CH:53]=[CH:52][C:51]=2[CH:55]([CH3:57])[CH3:56])=[O:26])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 380024-Nonylbenzoic acidHCID 123414Diphenylphosphoryl azide

Product 1

HCID 9845158HCID 9845158, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a 10 ml toluene solution of 1.0 g (4.04 mmol) of 4-nonylbenzoic acid was added 0.66 ml (4.28 mmol) of triethylamine. After stirring at room temperature for 15 minutes, 0.89 ml (4.12 mmol) of DPPA (diphenoxy phosphoryl azide) was added to the mixture. The whole was heated for 2 hours under reflux and then cooled to room temperature. After the addition of 0.77 ml (4.08 mmol) of 2,6-diisopropylaniline, the reaction mixture was stirred for 16 hours and then concentrated. The residue was purified by subjecting it to column chromatography over silica gel (eluent: n-hexane/chloroform=1/1) to give 1.07 g (62% yield) of 1-(4-nonylphenyl)-3-(2,6-diisopropylphenyl)urea, the physical properties of which being shown in the following Table 3. The compounds No. 5, No. 6, No. 7, No. 8, No. 9, No. 10, No. 12, No. 16, No. 20, No. 21, No. 22, No. 23, and No. 26 listed in Table 3 were similarly prepared as above.

Workup

  1. temperatureThe whole was heated for 2 hours
  2. temperatureunder reflux
  3. temperaturecooled to room temperature
  4. stirringthe reaction mixture was stirred for 16 hours
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-31c8a23e550547048f9ab75b74705bf2
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05063247

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes