4-Nitrobenzyl chloride → HCID 20086966, compound

HRID 1608655Notes

Reaction equation

HRID 1608655 reaction equation
[Cl:1][C:2]1[C:3](=[O:19])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[N:5]=[CH:6][C:7]=1[Cl:8].[N+](C1C=CC(CCl)=CC=1)([O-])=O.NC1C=CC(CN2C(=O)C(Cl)=C(Cl)C=N2)=CC=1.[CH3:48][S:49](Cl)(=[O:51])=[O:50]>C(O)(=O)C.N1C=CC=CC=1.[Fe]>[Cl:1][C:2]1[C:3](=[O:19])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:49]([CH3:48])(=[O:51])=[O:50])=[CH:12][CH:11]=2)[N:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 74824-Nitrobenzyl chlorideHCID 31297Methanesulfonyl chlorideHCID 2092246HCID 2092246, compoundHCID 20087000HCID 20087000, compound

Product 1

HCID 20086966HCID 20086966, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

4.5 g (15 mmoles) of 4,5-dichloro-2-(4-nitrobenzyl)-3(2H)-pyridazinone (prepared according to method III but using 4-nitrobenzyl chloride instead of 3-phenyl-2-propenyl chloride (M.P. 128-130 celsius)) are dissolved in 150 ml of 99.5% acetic acid solution. Then 7.5 g of iron dust are added to the solution at such a rate that the temperature should not exceed 20° C., and the suspension is stirred at room temperature for 8 hours. By working up the reaction mixture in the usual manner 3.15 g (77%) of 2-(4-aminobenzyl)-4,5-dichloro-3(2H)-pyridazinone melting at 187°-189° C. are obtained, which is dissolved in 34 ml of anhydrous pyridine. To the solution 1.24 ml (16 moles) of methanesulfonyl chloride are dropped under stirring and cooling at such a rate that the inner temperature should remain between 0° C. and 5° C. The mixture is then stirred at room temperature for 4 hours and poured onto water. The separated crystals are filtered and washed with water. Thus 2.34 g (57%) of the desired compound are obtained. M.p.: 152°-154° C.

Workup

  1. customexceed 20° C.
  2. customare obtained
  3. stirringunder stirring
  4. temperaturecooling at such a rate that the inner temperature
  5. customshould remain between 0° C. and 5° C
  6. stirringThe mixture is then stirred at room temperature for 4 hours
  7. additionpoured onto water
  8. filtrationThe separated crystals are filtered
  9. washwashed with water

Sources & evidence

ORD record
ord-ca17c4b6901d440095fd5a8fe126420b
Source dataset
uspto-grants-1995_03
Patent number
US05395934

Reaction notes

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