Diethylamine → N,N-diethyl-N'-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydrophthalamide

HRID 1902183Notes

Reaction equation

HRID 1902183 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=2[C:10]1=[O:19].[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>CC(C)=O>[CH2:20]([N:22]([CH2:23][CH3:24])[C:10](=[O:19])[C:11]1[CH2:18][CH2:17][CH2:16][CH2:15][C:12]=1[C:13]([NH:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[F:1])=[O:14])[CH3:21]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 1859312-(4-Chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-1h-isoindole-1,3(2h)-dione

Product 1

HCID 12893023N,N-diethyl-N'-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydrophthalamideYield 56.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 50 ml of acetone is dissolved 2.8 g of N-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide. To the solution is added 0.8 g of diethylamine under stirring at room temperature. After further stirring for 30 minutes, the solution is concentrated to dryness under reduced pressure, followed by adding 50 ml of n-hexane to cool. The resultant crystals are recovered by filtration and recrystallized from n-hexane, to yield 2.0 g of the subject compound. Melting point: 105° C.-106° C.

Workup

  1. stirringAfter further stirring for 30 minutes
  2. concentrationthe solution is concentrated to dryness under reduced pressure
  3. additionby adding 50 ml of n-hexane
  4. temperatureto cool
  5. filtrationThe resultant crystals are recovered by filtration
  6. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-693e37d947c9459e8046f38b26fc7757
Source dataset
uspto-grants-1982_12
Patent number
US04362546

Reaction notes

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