Bromazepam → 7-bromo-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-1-acetic acid methyl ester

HRID 1580606Notes

Reaction equation

HRID 1580606 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.C[O-].[Na+].CN(C)C=O.Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>O.C1(C)C=CC=CC=1>[CH3:33][O:32][C:30](=[O:31])[CH2:29][N:11]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:19][C:6]=2[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:8][CH2:9][C:10]1=[O:12]

Participants

7

Reactant 4

HCID 2441BromazepamHCID 6228DimethylformamideHCID 60984Methyl bromoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 545262157-bromo-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-1-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 0.1 mole of 7-bromo-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepin-2-one and 0.11 mole of sodium methoxide in about 200 ml. of dimethylformamide is heated at about 95° c. for about 20 minutes. To the mixture is added a solution of 0.11 mole of methyl bromoacetate in about 200 ml. of toluene over a period of about 1 hour at about 95° C., and heating is continued for an additional period of about 6 hours. The reaction mixture is then evaporated in vacuo and the residue thus obtained is stirred with about 500 ml. of water. The resulting suspension is filtered and the solids thus obtained are crystallized from a suitable organic solvent such as ether, methanol, methylene chloride, methylene chloridemethanol and the like to obtain 7-bromo-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-1-acetic acid methyl ester.

Workup

  1. temperatureheating
  2. waitis continued for an additional period of about 6 hours
  3. customThe reaction mixture is then evaporated in vacuo
  4. customthe residue thus obtained
  5. filtrationThe resulting suspension is filtered
  6. customthe solids thus obtained
  7. customare crystallized from a suitable organic solvent such as ether, methanol, methylene chloride, methylene chloridemethanol

Sources & evidence

ORD record
ord-5c59a8a07fd24e6195b2d36fa8a49e97
Source dataset
uspto-grants-1976_01
Patent number
US03933816

Reaction notes

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