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

HRID 355359
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 150529152-(4-Chlorophenyl)-2-(2,6-dichloro-4-nitrophenyl)acetonitrile2×HCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst
HCID 887
Methanol
Solvent
2×

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05830893

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes