Ethyl isocyanate → HCID 67172547, compound

HRID 1891258Notes

Reaction equation

HRID 1891258 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][CH2:8][C:9]([O:11]C)=O)=[C:4]([Cl:15])[CH:3]=1.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17]>C(Cl)Cl>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:8][C:9](=[O:11])[N:18]([CH2:16][CH3:17])[C:19]2=[O:20])=[C:4]([Cl:15])[CH:3]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 67172912HCID 67172912, compound

Product 1

HCID 67172547HCID 67172547, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-bromo-2-chlorobenzylamino)acetate (2C3) (1.44 mmol, 420 mg) was dissolved in DCM (35 ml) and ethyl isocyanate (2C4) (2.87 mmol, 0.227 ml, 204 mg) added. The mixture was stirred at room temperature overnight. The mixture was concentrated and azeotroped with DCM three times and then re-dissolved in DCM (10 ml) and TFA (3 ml) added. The solution was stirred for 1.5 h then quenched with saturated sodium carbonate solution and the phases separated. The aqueous layer was washed with DCM twice and the combined organics dried over sodium sulphate, filtered and concentrated to give 1-(4-bromo-2-chlorobenzyl)-3-ethylimidazolidine-2,4-dione (2C5) 430 mg (90%); 1H NMR (400 MHz, CDCl3) δ 7.58 (s, 1H) 7.42 (d, 1H) 7.22 (d, 1H) 4.65 (s, 2H) 3.79 (s, 2H) 3.59 (q, 2H) 1.23 (t, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customazeotroped with DCM three times
  3. dissolutionre-dissolved in DCM (10 ml)
  4. additionTFA (3 ml) added
  5. stirringThe solution was stirred for 1.5 h
  6. customthen quenched with saturated sodium carbonate solution
  7. customthe phases separated
  8. washThe aqueous layer was washed with DCM twice
  9. dry with materialthe combined organics dried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d6200d508d2448a8b119926338acc4e8
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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