Hydrochloric Acid → HCID 15087823, compound

HRID 1073181Notes

Reaction equation

HRID 1073181 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([NH:9][C:10](=[O:12])[CH3:11])=[C:4]([Cl:13])[CH:3]=1.S1C=[CH:17][CH:16]=[CH:15]1.[F-].[K+].Cl.[H][H]>CO.[Pt].CC(O)C.CC(=O)C>[Cl:13][C:4]1[CH:3]=[C:2]([NH:1][CH:16]([CH3:17])[CH3:15])[CH:7]=[C:6]([Cl:8])[C:5]=1[NH:9][C:10](=[O:12])[CH3:11]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 8030ThiopheneHCID 256806N-(4-Amino-2,6-dichlorophenyl)ethanimidic acidHCID 522689Potassium FluorideHCID 178418361HCID 178418361, compound

Product 1

HCID 15087823HCID 15087823, compoundYield 66.7%

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 180AcetoneSolventHCID 887MethanolSolvent2×HCID 3776IsopropanolSolvent

Procedure

A mixture of 20 parts of N-(4-amino-2,6-dichlorophenyl)acetamide, 10 parts of 2-propanone, 2 parts of a solution of thiophene in methanol 4%, 400 parts of methanol, 5 parts of potassium fluoride and 18 parts of 2-propanol, saturated with hydrogen chloride was hydrogenated in a Parr apparatus and at 50° C. with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 15.7 parts (66.7%) of N-[2,6-dichloro-4-[(1-methylethyl)amino]phenyl]acetamide (int. 98).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from acetonitrile
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-c429f1bf49c140dab93c83a8a7f98366
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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