Hydrochloric Acid → HCID 15052915, compound

HRID 868303Notes

Reaction equation

HRID 868303 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 sodium hydroxide solution 50%, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 360 parts of tetrahydrofuran was added dropwise, during a 5 minute period, a solution of 33.3 parts of 4-chlorobenzeneacetonitrile in 90 parts of tetrahydrofuran. Upon completion, stirring was continued for 4 hours at 50° C. The reaction mixture was poured into 1500 parts of crushed ice and acidified with concentrate hydrochloric acid. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried, yielding 63.8 parts (93.3%) of 2,6-dichloro-α-(4-chlorophenyl)-4-nitrobenzeneacetonitrile (intermediate 3).

Workup

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

Sources & evidence

ORD record
ord-117d25d03b7e4a3787c11890557f93bc
Source dataset
uspto-grants-1988_10
Patent number
US04778887

Reaction notes

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