1,2,3,6-Tetrahydrophthalimide → N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-1,2,3,6-tetrahydrophthalimide

HRID 1973449

Reaction equation

HRID 1973449 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[CH:3]2[CH2:7][CH:8]=[CH:9][CH2:10][CH:2]12.[K].S(C1C=CC(C)=CC=1)(O)(=O)=O.O[CH2:25][CH2:26][N:27]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][N:29]=[C:28]1[CH3:35]>>[CH3:35][C:28]1[N:27]([CH2:26][CH2:25][N:5]2[C:1](=[O:11])[CH:2]3[CH2:10][CH:9]=[CH:8][CH2:7][CH:3]3[C:4]2=[O:6])[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][N:29]=1

Participants

4

Reactant 3

HCID 68081,2,3,6-TetrahydrophthalimideHCID 5462222PotassiumHCID 867342581-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole tosylate

Product 1

HCID 21491658N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-1,2,3,6-tetrahydrophthalimide

Procedure

1,2,3,6-Tetrahydrophthalimide is converted to the potassium salt and reacted with 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole tosylate according to the procedure described in Example 13. The crude reaction mixture obtained is concentrated and the concentrate distributed between water and toluene. The toluene layer is separated and the solvent is evaporated to leave a residue which is recrystallized from 2-propanol, affording N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-1,2,3,6-tetrahydrophthalimide melting at about 118°-123° C.

Workup

  1. customThe crude reaction mixture
  2. customobtained
  3. concentrationis concentrated
  4. customThe toluene layer is separated
  5. customthe solvent is evaporated
  6. customto leave a residue which
  7. customis recrystallized from 2-propanol

Sources & evidence

ORD record
ord-90b718b0ea0140c8a9bcde1fb2cba8b1
Source dataset
uspto-grants-1976_12
Patent number
US03997572

Linked notes

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