Hydrochloric Acid → HCID 54402964, compound

HRID 1730830Notes

Reaction equation

HRID 1730830 reaction equation
Cl.[N:2]([O-])=O.[Na+].Cl.C([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C(=O)C)=[CH:13][C:12]=1[CH2:21][CH2:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)(=O)C.C([O-])(=O)C.[Na+].[C:35]([CH2:37][C:38]([C:40]1[O:41][CH:42]=[CH:43][CH:44]=1)=[O:39])#[N:36]>C(O)C.O>[O:39]=[C:38]([C:40]1[O:41][CH:42]=[CH:43][CH:44]=1)[CH:37]([N:2]=[N:27][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[OH:10])=[CH:29][CH:28]=1)[C:35]#[N:36]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1416712-FuroylacetonitrileHCID 517045Sodium AcetateHCID 203325085595-27-7HCID 23668193Sodium Nitrite

Product 1

HCID 54402964HCID 54402964, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

By utilizing 350 ml of water, 20 ml of 35% hydrochloric acid and 8 g of sodium nitrite, 35 g of 4-(2,5-bisacetoxyphenylethyl)aniline hydrochloride disclosed in Japanese Pat. Publication No. 444/63 was diazotized. Then, the mixture was neutralized with sodium acetate to adjust the pH of the solution to 6, and the mixture cooled with ice water was added dropwise at 5° C or less to liquid comprising of 13.5 g of 2-cyanoacetylfuran and 300 ml of ethanol. The resulting resinous substance was washed with water and decanted 2 times and then stirred in water, whereby crystals were formed. In 400 ml of ethanol, 40 g of the crude product obtained by filtering the crystals and drying the crystals was suspended. To the suspension, a liquid comprising 40 g of potassium hydroxide and 100 ml of water was added under vacuum, and the mixture heated for several minutes at 60° C, and then rapidly cooled. To the cooled mixture, 200 ml of a 35% hydrochloric acid aqueous solution was added to form crystals which were filtered, washed with water and recrystallized from 250 ml of ethanol to provide 19.5 g of the compound having a melting point of 175° to 178° C.

Workup

  1. washThe resulting resinous substance was washed with water
  2. customdecanted 2 times
  3. customwhereby crystals were formed
  4. filtrationby filtering the crystals
  5. customdrying the crystals
  6. additionTo the suspension, a liquid comprising 40 g of potassium hydroxide and 100 ml of water was added under vacuum
  7. temperaturerapidly cooled
  8. additionTo the cooled mixture, 200 ml of a 35% hydrochloric acid aqueous solution was added
  9. customto form crystals which
  10. filtrationwere filtered
  11. washwashed with water
  12. customrecrystallized from 250 ml of ethanol

Sources & evidence

ORD record
ord-dc75089b0e754d48b1ab5268afa94d1b
Source dataset
uspto-grants-1976_11
Patent number
US03994731

Reaction notes

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