4-Tert-Butylaniline → HCID 66603157, compound

HRID 751003Notes

Reaction equation

HRID 751003 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([O:13]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH:5]=1.[C:24]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([NH:32][C:31]2[CH:33]=[CH:34][C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:29][CH:30]=2)=[O:13])[CH:5]=1

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 19081261HCID 19081261, compound

Product 1

HCID 66603157HCID 66603157, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl-3-[N-(4-nitrophenoxycarbonyl)amino]benzoate (0.19 g, 0.60 mmol) and 4-tert-butylaniline (0.10 mL, 0.60 mmol) in pyridine (5 mL) was heated to reflux for 16 h. The solution was cooled and evaporated, and the residual material was taken up in ethyl acetate (100 mL). This was washed with 1 N aq. sodium hydroxide and brine, dried over magnesium sulfate, filtered and evaporated. The residual solid was triturated with ether, collected by filtration and dried under vacuum to afford the product, methyl-3-[3-(4-tert-butylphenyl)-ureido]-benzoate, as a solid (0.19 g, 0.58 mmol, 97%).

Workup

  1. temperatureto reflux for 16 h
  2. temperatureThe solution was cooled
  3. customevaporated
  4. washThis was washed with 1 N aq. sodium hydroxide and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual solid was triturated with ether
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-38d8172ec4bf48b8b045bcbe594b0822
Source dataset
uspto-grants-2008_07
Patent number
US07405233B2

Reaction notes

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