m-Tolyl isocyanate → N-tert-butyl-2-[3-(3-(3-tolyl)ureido)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl]ethanoic acid amide

HRID 263482Notes

Reaction equation

HRID 263482 reaction equation
[C:1]([NH:5][C:6](=[O:27])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10]([NH2:25])[C:9]1=[O:26])([CH3:4])([CH3:3])[CH3:2].[C:28]1([CH3:37])[CH:33]=[CH:32][CH:31]=[C:30]([N:34]=[C:35]=[O:36])[CH:29]=1>C(Cl)Cl>[C:1]([NH:5][C:6](=[O:27])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10]([NH:25][C:35]([NH:34][C:30]2[CH:29]=[C:28]([CH3:37])[CH:33]=[CH:32][CH:31]=2)=[O:36])[C:9]1=[O:26])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 15203365N-tert-butyl-2-(3-amino-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl) ethanoic acid amide

Product 1

HCID 15203358N-tert-butyl-2-[3-(3-(3-tolyl)ureido)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl]ethanoic acid amideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 25 ml round-bottomed flask equipped with N2 inlet were added N-tert-butyl-2-[3-amino-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl]ethanoic acid amide (0.50 g, 1.368 mmoles) and 10 ml methylene chloride under nitrogen, and the reaction cooled in an ice bath. A solution of m-tolyl isocyanate (0.194 ml, 1.5 mmol) in 5 ml methylene chloride was then added dropwise. A solid formed immediately. Stirring was continued for 15 minutes and then the ice bath removed, allowing the reaction to come to room temperature for several hours. The solid was filtered and washed with methylene chloride/hexane (1:1), yielding 600 mg (87.9%) of product, mp 263°-266° C.

Workup

  1. customTo a 25 ml round-bottomed flask equipped with N2 inlet
  2. temperaturethe reaction cooled in an ice bath
  3. customA solid formed immediately
  4. customthe ice bath removed
  5. customthe reaction
  6. waitto come to room temperature for several hours
  7. filtrationThe solid was filtered
  8. washwashed with methylene chloride/hexane (1:1)

Sources & evidence

ORD record
ord-b5face8acb88445caa67f5ea0441bbb4
Source dataset
uspto-grants-1997_07
Patent number
US05643904

Reaction notes

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