Hydrochloric Acid → HCID 15052915, compound

HRID 355358Notes

Reaction equation

HRID 355358 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1Cl.[OH-].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[Cl:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[CH:22]([C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)[C:23]#[N:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 883653,4,5-TrichloronitrobenzeneHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 15052915HCID 15052915, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 45.3 parts of 1,2,3-trichloro-5-nitrobenzene, 300 parts of a 50% aqueous sodium hydroxide solution, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 360 parts of tetrahydrofuran is added dropwise, during a 5 minutes period, a solution of 33.3 parts of 4-chlorobenzene-acetonitrile in 90 parts of tetrahydrofuran. Upon completion, stirring is continued for 4 hours at 50 degrees C. The reaction mixture is poured into 1500 parts of crushed ice and acidified with concentrate hydrochloric acid. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried, yielding 63.8 parts (93.3%) of 2,6-dichloro-α-(4-chlorophenyl)-4-nitrobenzeneacetonitrile (intermediate 1).

Workup

  1. additionis added dropwise, during a 5 minutes period
  2. additionThe reaction mixture is poured into 1500 parts of crushed ice
  3. extractionThe product is extracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe residue is stirred in 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-c1e52230aa614b2d9f0793afcddca6df
Source dataset
uspto-grants-1998_11
Patent number
US05830893

Reaction notes

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