2-Fluorobenzylamine → HCID 54250073, compound

HRID 232093Notes

Reaction equation

HRID 232093 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH3:10][O:11][C:12](=[O:20])[C:13]([N+:18]#[C-:19])=[CH:14]N(C)C>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH3:10][O:11][C:12]([C:13]1[N:18]=[CH:19][N:5]([CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[F:1])[CH:14]=1)=[O:20]

Participants

5

Reactant 2

HCID 666492-FluorobenzylamineHCID 2734778METHYL 3-(DIMETHYLAMINO)-2-ISOCYANOACRYLATE

Product 1

HCID 54250073HCID 54250073, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

8 g of o-fluorobenzylamine and 6.6 g of 2-isocyano-3-dimethylaminoacrylic acid methyl ester are dissolved in 66 ml of xylene and heated under reflux for 3 hours while stirring. After cooling to room temperature, the whole is diluted with ethyl acetate and extracted by shaking twice with 50 ml of 2N hydrochloric acid each time and then with water. The aqueous phases are washed twice with 50 ml of ethyl acetate each time. All the aqueous phases are combined, rendered alkaline with concentrated ammonia and then extracted by shaking three times with 100 ml of dichloromethane each time. The extracts are combined, washed twice with water, dried over magnesium sulphate and concentrated to dryness by evaporation. The residue is dissolved in ethyl acetate, filtered over silica gel, concentrated and caused to crystallise by the addition of diethyl ether. 1-(o-fluorobenzyl)-imidazole-4-carboxylic acid methyl ester having a melting point of 87°-89° is obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted
  4. stirringby shaking twice with 50 ml of 2N hydrochloric acid each time
  5. washThe aqueous phases are washed twice with 50 ml of ethyl acetate each time
  6. extractionextracted
  7. stirringby shaking three times with 100 ml of dichloromethane each time
  8. washwashed twice with water
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated to dryness by evaporation
  11. dissolutionThe residue is dissolved in ethyl acetate
  12. filtrationfiltered over silica gel
  13. concentrationconcentrated
  14. customto crystallise by the addition of diethyl ether

Sources & evidence

ORD record
ord-d954a0d841c1494baa93714cabe3a9ac
Source dataset
uspto-grants-1989_07
Patent number
US04851424

Reaction notes

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