HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dichloromethane → 5-[N-Benzyl-N-(3-chloro propyl)amino]-4-chloro-2-methyl-3(2H)-pyridazinone

HRID 394451
Notes
Print preview

Reaction equation

HRID 394451 reaction equation
[CH2:1]([N:8]([C:13]1[CH:18]=[N:17][N:16]([CH3:19])[C:15](=[O:20])[C:14]=1[Cl:21])[CH2:9][CH2:10][CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22]CCl.S(Cl)(Cl)=O>CN(C1C=CN=CC=1)C>[CH2:1]([N:8]([C:13]1[CH:18]=[N:17][N:16]([CH3:19])[C:15](=[O:20])[C:14]=1[Cl:21])[CH2:9][CH2:10][CH2:11][Cl:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 181764695-[N-Benzyl-N-(3-hydroxypropyl)amino]-4-chloro-2-methyl-3(2H)-pyridazinone

Product 1

HCID 181764675-[N-Benzyl-N-(3-chloro propyl)amino]-4-chloro-2-methyl-3(2H)-pyridazinoneYield 95%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridine
Catalyst

Procedure

To a solution of 10.00 g (32 mmol) of 5-[N-benzyl-N-(3-hydroxypropyl)amino]-4-chloro-2-methyl-3(2H)-pyridazinone in 100 ml of dichloromethane 3.5 ml (5.5 g, 46 mmol) of thionyl chloride are added dropwise while stirring. If necessary, a catalytic amount of 4-(N,N-dimethyl amino)pyridine is added to the solution. The reaction mixture is boiled for 14 hours, then cooled and evaporated. The evaporation residue is triturated with diethyl ether. The crystals are filtered off and washed with diethyl ether. In this way 9.50 g (95%) of the title compound are obtained with a melting point of 92-93° C.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe evaporation residue is triturated with diethyl ether
  4. filtrationThe crystals are filtered off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f256bd3f0be3411b97914b5dd7ee4c4e
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06602865B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes