Ethylenediamine → 9-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one

HRID 1532441Notes

Reaction equation

HRID 1532441 reaction equation
Br[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[CH2:15]([NH2:18])[CH2:16][NH2:17]>C(O)CCC>[N+:12]([C:11]1[C:2]2[NH:18][CH2:15][CH2:16][NH:17][C:4](=[O:6])[C:3]=2[CH:8]=[CH:9][CH:10]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 79263Methyl 2-bromo-3-nitrobenzoate

Product 1

HCID 27716119-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 11.7 parts of methyl 2-bromo-3-nitrobenzoate, 8.1 parts of 1,2-ethanediamine mononohydrate and 40 parts of 1-butanol was stirred for ½ hour at reflux temperature. The reaction mixture was evaporated and the residue was diluted with 50 parts of water. The precipitate was filtered off and washed with water and 2-propanol. It was then recrystallized from 2-methoxyethanol, yielding 6.5 parts of 2,3,4,5-tetrahydro-9-nitro-1H-1,4-benzodiazepin-5-one; m.p. 191-195° C. (interm. 1).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionthe residue was diluted with 50 parts of water
  4. filtrationThe precipitate was filtered off
  5. washwashed with water and 2-propanol
  6. customIt was then recrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-958a4b013bed4eb6b3158dfd6ff59bdb
Source dataset
uspto-grants-2001_03
Patent number
US06201119B1

Reaction notes

Loading…