Thiophene → HCID 13770358, compound

HRID 1249364Notes

Reaction equation

HRID 1249364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[Cl:21])([CH3:11])[C:9]#[N:10])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].S1C=CC=C1.[H][H]>CO.[Pt]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:22]([F:25])([F:23])[F:24])[CH:4]=2)([CH3:11])[C:9]#[N:10])=[C:13]([Cl:21])[CH:14]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 14301772HCID 14301772, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13770358HCID 13770358, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 31.1 parts of 4-chloro-α-(2-chloro-4-nitrophenyl)-α-methyl-3-(trifluoromethyl)benzeneacetonitrile, 2 parts of a solution of thiophene in methanol 4% and 480 parts of methanol was hydrogenated in the Parr apparatus at 50° C. with 3 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off, washed with tetrahydrofuran and the filtrate was evaporated in vacuo. The residue was crystallized from 160 parts of 2-propanol. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 23.7 parts (82.4%) of (4-amino-2-chloro-α-[4-chloro-3-(trifluoromethyl)phenyl]-α-methylbenzeneacetonitrile; mp. 180.4° C. (intermediate 26).

Workup

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

Sources & evidence

ORD record
ord-567303d5823a4fa195ef91a9b86eef21
Source dataset
uspto-grants-1986_12
Patent number
US04631278

Reaction notes

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