Methanol → 4,4'-Bis(4-aminobenzamido)-3,3'-dihydroxybiphenyl

HRID 2396867

Reaktionsgleichung

Reaktionsgleichung von HRID 2396867
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([OH:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].C([N:19]([CH2:22][CH3:23])CC)C.[N+:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([O-])=O.[CH3:36][OH:37]>O1CCCC1.CN(C)C=O>[NH2:24][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][C:7]([NH:8][C:36](=[O:37])[C:2]4[CH:3]=[CH:23][C:22]([NH2:19])=[CH:6][CH:7]=4)=[C:2]([OH:1])[CH:3]=3)=[CH:10][C:11]=2[OH:16])=[O:32])=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 169183,3'-Dihydroxybenzidine

Produkt 1

HCID 189864474,4'-Bis(4-aminobenzamido)-3,3'-dihydroxybiphenylAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

35.0 g (0.162 moles) of 3,3'-dihydroxy-4,4'-diaminobiphenyl and 36.0 g (0.356 moles) of triethylamine were dissolved in a mixed solvent of 300 ml of tetrahydrofuran and 300 ml of N,N-dimethylformamide (DMF) and cooled down to 0° C. Thereafter, a solution of 63.1 g (0.340 moles) of p-nitrobenzoyl chloride in 150 ml of tetrahydrofuran was dropped in the solution in such a way that the resultant reaction solution had a temperature not higher than 10° C. Subsequently, the reaction solution was poured into one liter of methanol thereby permitting the resulting reaction product to be precipitated, followed by filtering, washing with tetrahydrofuran, then with water and finally with methanol, and drying to obtain crude red crystals of 4,4'-bis(4-aminobenzamido)-3,3'-dihydroxybiphenyl. The yield was 82.1 g (at a yield of 99.7%). The crude crystals were recrystallized from a mixed solvent of dimethylformamide and methanol to obtain a pure product.

Aufarbeitung

  1. customreaction solution
  2. customhigher than 10° C
  3. customthe resulting reaction product
  4. customto be precipitated
  5. filtrationby filtering
  6. washwashing with tetrahydrofuran
  7. dry with materialwith water and finally with methanol, and drying

Quellen und Nachweise

ORD-Eintrag
ord-360cd188f6e5401f8bc5216d044f15d7
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05494991

Verknüpfte Notizen

Wird geladen…