4-Chlorobutyryl chloride → HCID 20507190, compound

HRID 354681Notes

Reaction equation

HRID 354681 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][CH2:19][C:20](Cl)=[O:21]>C1(C)C=CC=CC=1>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]([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:21]

Participants

4

Reactant 2

HCID 783704-Chlorobutyryl chlorideHCID 161928Ici 109,081

Product 1

HCID 20507190HCID 20507190, compoundYield 93.3%

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 4.6 g (32.6 millimoles) of 4-chlorobutyryl chloride in 100 ml of absolute toluene are kept for 6 hours at 80° C. The product is filtered off at 10° C., washed with water and dried under reduced pressure at 50° C. 8.5 g (93% of theory) of 6-[p-(4-chlorobutyrylamino)-phenyl]-5-methyl-4,5-dihydropyridaz-3-one are obtained as beige crystals which, after recrystallization from methanol, melt at 176°-178° 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-da06bda69ff541b49c0652ef8be327c8
Source dataset
uspto-grants-1983_03
Patent number
US04376771

Reaction notes

Loading…