Water → HCID 13854009, compound

HRID 649309Notes

Reaction equation

HRID 649309 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[CH2:6][C:7]([CH3:9])=[O:8].[CH2:15](N)[CH2:16][CH2:17][CH3:18].C1(C)C=CC=CC=1.[OH2:27]>C(O)(=O)C>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[NH:4][C:5]([C:6]1[C:15](=[O:27])[CH:16]=[C:17]([CH3:18])[O:8][C:7]=1[CH3:9])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7156Acetoacetyl-2-chloroanilideHCID 8007Butylamine

Product 1

HCID 13854009HCID 13854009, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
60 °C

Procedure

A solution of 4.23 g (20 m mol) of o-chloroacetoacetanilide, 1.46 g (20 m mol) of n-butylamine and 20 ml of toluene, after one drop of acetic acid was added, was stirred for 1.5 hours at 60° C. and was refluxed for 30 minutes while resulted water was distilled off from the reaction mixture together with about 10 ml of toluene. After 8.10 g (80 m mol) of triethylamine was added, a solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes and the reaction mixture was further refluxed for 2 hours. The reaction mixture was heated to distill off about 12 ml of solvent from the reaction mixture and was cooled to room temperature. The resulting crystals were filtered off, washed and dried under reduced pressure to obtain 1.59 g of the title compound. (Yield: 29%).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. distillationwas distilled off from the reaction mixture together with about 10 ml of toluene
  3. additionAfter 8.10 g (80 m mol) of triethylamine was added
  4. additiona solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes
  5. temperaturethe reaction mixture was further refluxed for 2 hours
  6. temperatureThe reaction mixture was heated
  7. distillationto distill off about 12 ml of solvent from the reaction mixture
  8. temperaturewas cooled to room temperature
  9. filtrationThe resulting crystals were filtered off
  10. washwashed
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-735866379f464a3492a3ffc18ce982c4
Source dataset
uspto-grants-1988_04
Patent number
US04739083

Reaction notes

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