Hydrochloric Acid → HCID 12569777, compound

HRID 1154926Notes

Reaction equation

HRID 1154926 reaction equation
[N+](=[CH:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17](=[O:21])[CH:18]=[N+]=[N-])=[CH:10][CH:9]=1)=[N-].[Cl-:23].[Na+].[ClH:25]>CO>[Cl:23][CH2:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17](=[O:21])[CH2:18][Cl:25])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 54519946HCID 54519946, compound

Product 1

HCID 12569777HCID 12569777, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

About 42 millimoles of the 1,4-bis-(5'-diazo-4'-oxopentyl)-benzene obtained from the preceding reaction, dissolved in 190 ml of methanol, are slowly added dropwise to a mixture of 117 ml of 5 M sodium chloride solution and 117 ml of 2 N hydrochloric acid solution, with vigorous stirring. The mixture turns cloudy and gas is evolved. Stirring is continued for 30 minutes and the yellow crude product which has precipitated (18.3 g) is filtered off. It is chromatographed over a silica gel column (length 30 cm, diameter 7 cm), using chloroform as the mobile phase, and colorless crystals are obtained; these are recrystallized from isopropanol. 1,4-bis-(5'-Chloro-4'-oxopentyl)-benzene is obtained in 51% yield (6.7 g); melting point 70°-71° C.

Workup

  1. customthe yellow crude product which has precipitated (18.3 g)
  2. filtrationis filtered off
  3. customIt is chromatographed over a silica gel column (length 30 cm, diameter 7 cm)
  4. customare obtained
  5. customthese are recrystallized from isopropanol

Sources & evidence

ORD record
ord-807cff686c604d9ea62c9d6827ec3e27
Source dataset
uspto-grants-1981_11
Patent number
US04298751

Reaction notes

Loading…