Methoxyacetyl chloride → HCID 13193372, compound

HRID 463648Notes

Reaction equation

HRID 463648 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][O:17][CH2:18][C:19](Cl)=[O:20]>O1CCCC1>[CH3:16][O:17][CH2:18][C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:20]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 161928Ici 109,081

Product 1

HCID 13193372HCID 13193372, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (29.5 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 3.9 g (35.9 millimoles) of methoxyacetyl chloride in 150 ml of absolute tetrahydrofuran were refluxed for 2 hours, while stirring. The product was filtered off under suction at 10° C., washed with water and recrystallized from dimethylformamide/water. 3.6 g (44%) of 6-[p-(methoxyacetylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone were obtained as colorless crystals. Mp.: 212° C.

Workup

  1. filtrationThe product was filtered off under suction at 10° C.
  2. washwashed with water
  3. customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-033592ddf1424ce88f106ae14b20b8e5
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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