1,1'-Carbonyldiimidazole → 1,2,4,5-Tetrahydro-4-methyl-1-phenyl-3H-2,4-benzodiazepin-3-one

HRID 1769113Notes

Reaction equation

HRID 1769113 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:11].[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:18](=[O:19])[NH:11][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 149782392-[(Methylamino)methyl]-alpha-phenylbenzenemethanamine

Product 1

HCID 149782501,2,4,5-Tetrahydro-4-methyl-1-phenyl-3H-2,4-benzodiazepin-3-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 32.8 g (145 mmol) of 2-[(methylamino)methyl]-α-phenylbenzenemethanamine in 215 mL of chloroform was treated with 25.9 g (159 mmol) of carbonyldiimidazole. The reaction was stirred at room temperature for 19 hours, washed four times with water, dried over sodium sulfate and stripped in vacuo. The gummy residue was triturated in and recrystallized from ethyl acetate to yield 26 g (71%) of product, mp 198-199.

Workup

  1. washwashed four times with water
  2. dry with materialdried over sodium sulfate
  3. customThe gummy residue was triturated in and
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-58b09cce58db44e5a6faa14061ea2bdc
Source dataset
uspto-grants-1995_01
Patent number
US05380721

Reaction notes

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