Toluene → HCID 12688600, compound

HRID 1732650Notes

Reaction equation

HRID 1732650 reaction equation
[C:1]([C:4]1[C:5](=[O:24])[NH:6][N:7]=[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.Cl[CH2:39][CH2:40][N:41]([CH3:43])[CH3:42]>O.CN(C)C=O>[CH3:42][N:41]([CH3:43])[CH2:40][CH2:39][N:6]1[C:5](=[O:24])[C:4]([C:1](=[O:3])[CH3:2])=[C:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[N:7]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 43908775643-31-1

Product 1

HCID 12688600HCID 12688600, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one (20.0 g), potassium carbonate (9.0 g) and 30 ml of a toluene solution of N-(2-chloroethyl)dimethylamine (0.34 g/ml) and dimethylformamide (150 ml) were stirred at 80° C. for 18 hours. A second equivalent of the amine was added and heating continued for an additional four hours. The mixture was cooled, poured into water and the suspension extracted with ethyl acetate. The combined organic extracts were dried and evaporated in vacuo. Following purification by dry column silica gel chromatography and recrystallization, the title compound was obtained (63 percent yield), m.p. 149°-150° C.

Workup

  1. temperatureheating
  2. temperatureThe mixture was cooled
  3. extractionthe suspension extracted with ethyl acetate
  4. customThe combined organic extracts were dried
  5. customevaporated in vacuo
  6. custompurification
  7. customby dry
  8. customcolumn silica gel chromatography and recrystallization

Sources & evidence

ORD record
ord-16c4551636424c1e8b07a699de78b84c
Source dataset
uspto-grants-1980_12
Patent number
US04238490

Reaction notes

Loading…