Triethylamine → 4-[3-(3-Bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoic acid methyl ester

HRID 412437Notes

Reaction equation

HRID 412437 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)C(O)=O.C([N:13]([CH2:16]C)CC)C.[O:18](P(N=[N+]=[N-])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[CH3:37][O:38][C:39](=[O:60])[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][NH:47][C:48]2[CH:53]=[CH:52][C:51]([C:54]3[CH2:59][CH2:58][CH2:57][CH2:56][CH:55]=3)=[CH:50][CH:49]=2)=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:37][O:38][C:39](=[O:60])[C:40]1[CH:41]=[CH:42][C:43]([CH2:46][N:47]([C:48]2[CH:53]=[CH:52][C:51]([C:54]3[CH2:59][CH2:58][CH2:57][CH2:56][CH:55]=3)=[CH:50][CH:49]=2)[C:16]([NH:13][C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)=[O:18])=[CH:44][CH:45]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 114563-Bromobenzoic acidHCID 123414Diphenylphosphoryl azideHCID 16067949HCID 16067949, compound

Product 1

HCID 674834554-[3-(3-Bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To 3-bromobenzoic acid (1.2 g, 5.7 mmol) in toluene (20 mL) was added triethylamine (0.91 mL, 6.5 mmol) and diphenoxyphosphoryl azide (1.3 mL, 6.2 mmol) and the mixture was heated to 100° C. while stirring. After 1 hour 4-[(4-cyclohex-1-enylphenylamino)methyl]-benzoic acid methyl ester (prepared similarly as described in example 1, step 1) (1.6 g, 5 mmol) was added and heating was continued for additional 1.5 hour. After cooling to room temperature the mixture was transferred with ethyl acetate (50 mL) to a separatory funnel. The organic mixture was washed with saturated aqueous sodium hydrogen carbonate (2×50 mL), backwash with ethyl acetate (50 mL). The organic phases were collected, dried (sodium sulphate) and the solvent removed in vacuo to yield a brown oil that was purified on silica column eluted with DCM to afford 700 mg of 4-[3-(3-bromophenyl)-1-(4-cyclohex-1-enylphenyl)ureidomethyl]benzoic acid methyl ester.

Workup

  1. additionwas added
  2. temperatureheating
  3. temperatureAfter cooling to room temperature the mixture
  4. washThe organic mixture was washed with saturated aqueous sodium hydrogen carbonate (2×50 mL), backwash with ethyl acetate (50 mL)
  5. customThe organic phases were collected
  6. dry with materialdried (sodium sulphate)
  7. customthe solvent removed in vacuo
  8. customto yield a brown oil that
  9. customwas purified on silica column
  10. washeluted with DCM

Sources & evidence

ORD record
ord-200d6b7d7ff944a4a764fe15cbaeb8e8
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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