Water → HCID 13079858, compound

HRID 2418650Notes

Reaction equation

HRID 2418650 reaction equation
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].Cl[CH:16]=[C:17]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH:18]=O.O>CN(C)C=O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:16]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([C:9]([F:10])([F:11])[F:12])=[N:1][CH:18]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 53853578HCID 53853578, compound

Product 1

HCID 13079858HCID 13079858, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 3-amino-4,4,4-trifluorocrotonate (1.55 g; prepared by the method of Swarts, Bull. Sci. acad. roy. Belg., 1926, 12 (5), 679) in dry dimethylformamide (2 ml) was added dropwise to a suspension of sodium hydride (0.20 g) in dimethylformamide (20 ml). The mixture was then stirred for 30 minutes and 3-chloro-2-(p-chlorophenyl)prop-2-enal (1.7 g) was added dropwise. The mixture was stirred for 2 hours, allowed to stand overnight and poured into water. The resulting mixture was twice extracted with diethyl ether and the combined extracts washed with water, dried and filtered through charcoal. The filtrate was concentrated and the residue recrystallised from aqueous ethanol to give the title compound (1.1 g), m.p. 84°-5°.

Workup

  1. customprepared by the method of Swarts, Bull
  2. stirringThe mixture was stirred for 2 hours
  3. waitto stand overnight
  4. extractionThe resulting mixture was twice extracted with diethyl ether
  5. washthe combined extracts washed with water
  6. customdried
  7. filtrationfiltered through charcoal
  8. concentrationThe filtrate was concentrated
  9. customthe residue recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-5fd6a59819394f8cade7c2154077d7ea
Source dataset
uspto-grants-1984_09
Patent number
US04473395

Reaction notes

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