Hydrochloric Acid → 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline

HRID 1795207Notes

Reaction equation

HRID 1795207 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](N)[CH2:25][NH2:26].[OH-].[Na+].Cl>>[NH:26]1[CH2:25][CH2:24][N:12]=[C:11]1[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 121253-NitrophenylacetonitrileHCID 14798Sodium HydroxideHCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)

Product 1

HCID 113557923-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline

Conditions

Temperature
100 °C

Procedure

A mixture of 30.7 mmol (5 g) of 3-nitrophenylacetonitrile and 30 mmol (7.2 g) of ethylenediamine para-toluenesulphonate is heated at 100° C. for 1 hour. After cooling to 20° C., the mixture is hydrolysed with 100 ml of a 5M aqueous solution of sodium hydroxide and then extracted with dichloromethane. The organic phases are dried over magnesium sulphate and concentrated. The residue obtained is converted into the hydrochloride by the action of an ethanolic HCl solution to yield the expected product.

Workup

  1. temperatureAfter cooling to 20° C.
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phases are dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue obtained

Sources & evidence

ORD record
ord-a73103cc583e4d9fbb47f7e01d78c955
Source dataset
uspto-grants-2006_04
Patent number
US07026357B2

Reaction notes

Loading…