Acetonitrile → HCID 20358774, compound

HRID 2082930Notes

Reaction equation

HRID 2082930 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:28])[CH3:27])=[CH:22][C:21]=1[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[O:14].[Cl:36][C:37]([Cl:42])([Cl:41])[C:38](Cl)=[O:39].C(N(CC)CC)C.C(#N)C>O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:38](=[O:39])[C:37]([Cl:42])([Cl:41])[Cl:36])=[CH:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:27])[CH3:28])=[CH:22][C:21]=1[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[O:14]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 12525034HCID 12525034, compound

Product 1

HCID 20358774HCID 20358774, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14.3 g of 1-hydroxy-4-amino-N-[γ-(2,4-di-tert-amylphenoxy)propyl]-2-naphthamide obtained in Step (b) of Synthesis I, 6 g of trichloroacetyl chloride and 3.3 g of triethylamine were added to 300 ml of acetonitrile, and the mixture was refluxed for 4 hours. After conclusion of the reaction, the reaction solution was condensed to 100 ml and water was added thereto. The solution was then extracted with ethyl acetate. After removal of the ethyl acetate by distillation, n-hexane was added to the residue. The solid precipitate was separated by filtration and recrystallized from ethanol to obtain the object compound. Yield: 10 g. Melting point: 190° - 192° C.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customAfter conclusion of the reaction
  3. additionwas added
  4. extractionThe solution was then extracted with ethyl acetate
  5. customAfter removal of the ethyl acetate
  6. distillationby distillation, n-hexane
  7. additionwas added to the residue
  8. customThe solid precipitate was separated by filtration
  9. customrecrystallized from ethanol
  10. customto obtain the object compound

Sources & evidence

ORD record
ord-cd8db21af4244c56ba69da2b769a7398
Source dataset
uspto-grants-1978_04
Patent number
US04083721

Reaction notes

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