Toluene → HCID 19896212, compound

HRID 1196761Notes

Reaction equation

HRID 1196761 reaction equation
[NH2:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[CH:3][C:4]([O:6]CC)=O.[H-].[Na+].C1(C)C=CC=CC=1.[F:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[N:33]=[C:34]=[O:35]>CN(C)C=O>[F:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[N:33]1[C:4](=[O:6])[CH:3]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[NH:1][C:34]1=[O:35]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 45582034-Chloro-2-fluorophenyl isocyanateHCID 67835821Ethyl 3-amino-3-(2-fluorophenyl)-2-propenoate

Product 1

HCID 19896212HCID 19896212, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.1 g of this ethyl 3-amino-3-(2-fluorophenyl)-2-propenoate was added dropwise to a solution of 0.5 g of sodium hydride (purity: 55%) in 20 ml of dimethylformamide with stirring at 0° C. The resulting solution was further stirred at room temperature for 15 minutes and then cooled to -30° C. and added dropwise with 20 ml of a toluene solution of 1.7 g of 2-fluoro-4-chlorophenyl isocyanate. The resultant solution was heated to room temperature and stirred at 80° C. for 30 minutes. Then the solvent was distilled away under reduced pressure and 100 ml of water was added to the residue to dissolve it. This aqueous solution was washed twice with diethyl ether and added to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid. The precipitated crystals were filtered out and dried under the reduced pressure to obtain 3.0 g of a crude product. This crude product was washed with heated diisopropyl ether and then dried to obtain 2.4 g of the objective compound.

Workup

  1. stirringThe resulting solution was further stirred at room temperature for 15 minutes
  2. temperaturecooled to -30° C.
  3. stirringstirred at 80° C. for 30 minutes
  4. distillationThen the solvent was distilled away under reduced pressure and 100 ml of water
  5. additionwas added to the residue
  6. dissolutionto dissolve it
  7. washThis aqueous solution was washed twice with diethyl ether
  8. additionadded to a mixed solution of 50 g of ice and 20 ml of concentrated hydrochloric acid
  9. filtrationThe precipitated crystals were filtered out
  10. customdried under the reduced pressure
  11. customto obtain 3.0 g of a crude product
  12. washThis crude product was washed with heated diisopropyl ether
  13. customdried

Sources & evidence

ORD record
ord-ec1921e50158484d92c457c77ec54a77
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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