Water → HCID 14128624, compound

HRID 476819Notes

Reaction equation

HRID 476819 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7](=[O:12])[CH2:8][C:9]([CH3:11])=[O:10])=[CH:4][CH:3]=1.[CH2:15](N)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH2:23].[C:24]1([CH3:30])C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]([C:8]2[C:24](=[O:23])[CH:30]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:10][C:9]=2[CH3:11])=[O:12])=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 7504BenzylamineHCID 7587p-Chloroacetoacetanilide

Product 1

HCID 14128624HCID 14128624, compoundYield 77.5%

Procedure

A mixture of 2.12 g (10 m mol) of p-chloroacetoacetanilide, 1.07 g (10 m mol) of benzylamine and 20 ml of toluene was refluxed for 1 hour, while the resulted water together with about 12 ml of toluene were distilled off outside the reaction system. After the remaining solvent in the mixture was removed by a rotary evaporator under vacuo, 4.49 g (22 m mol) of 2,2-dimethyl-6-phenyl-4H-1,3-dioxin-4-one, 4.65 g (40 m mol) of N,N,N',N'-tetramethylethylenediamine and 20 ml of xylene were added to the residue. While further refluxing gently for 1.5 hours, the resulted acetone was removed to outside the reaction system. The mixture was cooled to precipitate the crystals. The crystals were filtered and dried to afford 2.63 g of the title compound (yield: 77.5%).

Workup

  1. distillationwere distilled off outside the reaction system
  2. customAfter the remaining solvent in the mixture was removed by a rotary evaporator under vacuo, 4.49 g (22 m mol) of 2,2-dimethyl-6-phenyl-4H-1,3-dioxin-4-one, 4.65 g (40 m mol) of N,N,N',N'-tetramethylethylenediamine and 20 ml of xylene
  3. additionwere added to the residue
  4. temperatureWhile further refluxing gently for 1.5 hours
  5. customthe resulted acetone was removed to outside the reaction system
  6. temperatureThe mixture was cooled
  7. customto precipitate the crystals
  8. filtrationThe crystals were filtered
  9. customdried

Sources & evidence

ORD record
ord-d00000d9f3b745b6a8467c6d78e552d5
Source dataset
uspto-grants-1989_12
Patent number
US04886546

Reaction notes

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