3-Chloropropionyl chloride → HCID 20507193, compound

HRID 354680Notes

Reaction equation

HRID 354680 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.[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C1(C)C=CC=CC=1>[Cl:16][CH2:17][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 693643-Chloropropionyl chlorideHCID 161928Ici 109,081

Product 1

HCID 20507193HCID 20507193, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g (29.6 millimoles) of 6-(p-aminophenyl)-5-methyl-4,5-dihydropyridaz-3-one and 4.1 g (32.3 millimoles) of 3-chloropropionyl chloride are stirred with 100 ml of absolute toluene for 4 hours at 80° C. The product is filtered off at 10° C., washed with water and dried under reduced pressure at 50° C. 5.8 g (67% of theory) of 6-[p-(3-chloropropionylamino)-phenyl]-5-methyl-4,5-dihydropyridaz-3-one are obtained as beige crystals which, after recrystallization from methanol, melt, with decomposition, at 221°-223° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed with water
  3. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-ef16faca24b54c56b9c0ed29931d90f7
Source dataset
uspto-grants-1983_03
Patent number
US04376771

Reaction notes

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