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Hydrochloric Acid → 4-[3-(3-Bromophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid

HRID 412434
Notes
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Reaction equation

HRID 412434 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl.[O:10]=[C:11](Cl)OC(Cl)(Cl)Cl.[CH:18]1([C:24]2[CH:29]=[CH:28][C:27]([NH:30][CH2:31][C:32]3[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(OCC)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:11](=[O:10])[N:30]([CH2:31][C:32]2[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=2)[C:27]2[CH:28]=[CH:29][C:24]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)=[CH:25][CH:26]=2)[CH:6]=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10426DiphosgeneHCID 115623-BromoanilineHCID 223111294-[(4-Cyclohexylphenylamino)methyl]benzoic acid

Product 1

HCID 223110904-[3-(3-Bromophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acidYield 94%

Reagents, catalysts & solvents 3

HCID 1140
Toluene
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

3-Bromoaniline (1.4 g, 8.1 mmol) was dissolved in diethyl ether (50 mL) and 3.5 M dry HCl in ethyl acetate (2.3 mL) was added. The mixture was concentrated in vacuo. The residue was added toluene (100 mL) and concentrated in vacuo. The residue was added toluene (100 mL) and diphosgene (8.1 g, 41 mmol) and the resulting mixture was refluxed for 1.5 hour. After cooling, the mixture was concentrated in vacuo. The residue was dissolved in toluene (100 mL) and concentrated in vacuo. The residue was dissolved in DMF (30 mL) and 4-[(4-cyclohexylphenylamino)methyl]benzoic acid (1.3 g, 4.1 mmol) was added. The mixture was stirred at room temperature for 16 hours. The mixture was added ethyl acetate (150 mL) and washed with water:brine (1:1) (2×100 mL). The organic phase was dried with sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting first with a mixture of ethyl acetate:n-heptane:triethylamine (7:2:1), then with ethyl acetate and finally with methanol to afford 1.95 g (94%) of 4-[3-(3-bromophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionThe residue was added toluene (100 mL)
  3. concentrationconcentrated in vacuo
  4. temperaturethe resulting mixture was refluxed for 1.5 hour
  5. temperatureAfter cooling
  6. concentrationthe mixture was concentrated in vacuo
  7. dissolutionThe residue was dissolved in toluene (100 mL)
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in DMF (30 mL)
  10. washwashed with water:brine (1:1) (2×100 mL)
  11. dry with materialThe organic phase was dried with sodium sulphate
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by column chromatography on silica gel eluting first with a mixture of ethyl acetate:n-heptane:triethylamine (7:2:1)

Sources & evidence

ORD record
ord-7de40279f20b4b09a980c482912b2c07
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562807B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes