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

HRID 54967Notes

Reaction equation

HRID 54967 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-f500d8a17ba74cfcbc33c035f86486e4
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

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