Thiophene → (4-Amino-2,6-dichlorophenyl)(4-chlorophenyl)acetonitrile

HRID 355359Notes

Reaction equation

HRID 355359 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[CH:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:13]#[N:14].S1C=CC=C1.[H][H]>CO.[Pt]>[NH2:8][C:6]1[CH:5]=[C:4]([Cl:11])[C:3]([CH:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:13]#[N:14])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 15052915HCID 15052915, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 15068435(4-Amino-2,6-dichlorophenyl)(4-chlorophenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 31.1 parts of 2,6-dichloro-α-(4-chlorophenyl)-4-nitrobenzeneacetonitrile (intermediate 1), 2 parts of a solution of 4% thiophene in methanol and 480 parts of methanol is hydrogenated in the Parr apparatus at 50 degrees C with 3 parts of 5% platinum-on-charcoal catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off, washed with tetrahydrofuran and the filtrate is evaporated in vacuo. The residue is crystallized from 160 parts of 2-propanol. The product is filtered off, washed with 2,2'-oxybispropane and dried, yielding 4-amino-2,6-dichloro-α-(4-chlorophenyl)benzeneacetonitrile. (intermediate 2).

Workup

  1. filtrationthe catalyst is filtered off
  2. washwashed with tetrahydrofuran
  3. customthe filtrate is evaporated in vacuo
  4. customThe residue is crystallized from 160 parts of 2-propanol
  5. filtrationThe product is filtered off
  6. washwashed with 2,2'-oxybispropane
  7. customdried

Sources & evidence

ORD record
ord-79d27a6612894597ba3cad69adab2702
Source dataset
uspto-grants-1998_11
Patent number
US05830893

Reaction notes

Loading…