Water → HCID 13854009, compound

HRID 649308Notes

Reaction equation

HRID 649308 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].Cl[C:16]1[CH:22]=CC=[CH:19][C:17]=1N.C1(C)C=CC=CC=1.[OH2:30]>Cl>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[NH:4][C:5]([C:6]1[C:19](=[O:30])[CH:17]=[C:16]([CH3:22])[O:8][C:7]=1[CH3:9])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7156Acetoacetyl-2-chloroanilideHCID 72402-Chloroaniline

Product 1

HCID 13854009HCID 13854009, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A mixture of 4.23 g (20 m mol) of o-chloroacetoacetanilide, 2.55 g (20 m mol) of o-chloroaniline and 20 ml of toluene, after adding one drop of hydrochloric acid was refluxed for 2 hours while the resulted water was distilled off from the reaction system together with about 10 ml of toluene. After 9.30 g (80 m mol) of N,N,N',N'-tetramethylethylenediamine was added to the remaining solution, a solution of 9.94 g (70 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in 25 ml of toluene was dropwise added over a period of 15 minutes.

Workup

  1. distillationwas distilled off from the reaction system together with about 10 ml of toluene
  2. additionAfter 9.30 g (80 m mol) of N,N,N',N'-tetramethylethylenediamine was added to the remaining solution
  3. additiona solution of 9.94 g (70 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in 25 ml of toluene was dropwise added over a period of 15 minutes

Sources & evidence

ORD record
ord-d3fd418e06084b518049b7523dff0509
Source dataset
uspto-grants-1988_04
Patent number
US04739083

Reaction notes

Loading…