Benzaldehyde → HCID 70205004, compound

HRID 321989Notes

Reaction equation

HRID 321989 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[C:15]([Cl:16])=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[Cl:17])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[N:20]([O-])=O.[Na+].O.O.[Sn](Cl)Cl.[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)(=O)C.O.Cl.C(Cl)(Cl)Cl>[C:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[C:15]([Cl:16])=[CH:14][C:12]([NH:13][N:20]=[CH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:11][C:10]=2[Cl:17])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 240BenzaldehydeHCID 61436Stannous chloride dihydrateHCID 22008583HCID 22008583, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 70205004HCID 70205004, compoundYield 65.3%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

In 10 ml of acetic acid was dissolved 1.0 g of 4-(4-Acetylbenzyl)-3,5-dichloroaniline. To the solution was then added 1.0 ml of 35% hydrochloric acid. To the mixture was added dropwise, while cooling at temperatures ranging from 8-10° C., a solution of 0.3 g of 98.5% sodium nitrite in 1.0 ml water. The reaction mixture was stirred for one hour under the same conditions, to which was then added 2.0 g of Tin (II) chloride dihydrate dissolved in 2.0 ml of 35% hydrochloric acid. The reaction mixture was stirred for 3 hours at room temperature. To the mixture then added 20 ml of water and 20 ml chloroform. To the mixture was added dropwise, while cooling at the temperatures ranging from 5-10° C., 0.36 g of benzaldehyde. The reaction mixture was stirred for 30 minutes under the same conditions. After completion of the reaction, followed by extraction with 20 ml of chloroform. The extract was washed with water and sturated sodium hydrogen carbonate solution, dried over an hydrous magnesium sulfate, and concentrated to provide 0.88 g of the title compound as a colorless crystals, m.p.137-139° C.

Workup

  1. additionTo the mixture was added dropwise
  2. temperaturewhile cooling at temperatures
  3. customranging from 8-10° C.
  4. stirringThe reaction mixture was stirred for 3 hours at room temperature
  5. additionTo the mixture was added dropwise
  6. temperaturewhile cooling at the temperatures
  7. customranging from 5-10° C.
  8. stirringThe reaction mixture was stirred for 30 minutes under the same conditions
  9. customAfter completion of the reaction
  10. extractionfollowed by extraction with 20 ml of chloroform
  11. washThe extract was washed with water and sturated sodium hydrogen carbonate solution
  12. dry with materialdried over an hydrous magnesium sulfate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-9c50a6ce96714621ac5e338b9ae9eb61
Source dataset
uspto-grants-2001_04
Patent number
US06211178B1

Reaction notes

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