Hydrochloric Acid → HCID 9914839, compound

HRID 429782Notes

Reaction equation

HRID 429782 reaction equation
[Na].[CH:2]1[CH:3]=[CH:4][C:5]2[C:6](=[CH:8][CH:9]=[CH:10][C:11]=2O)[CH:7]=1.CS([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[C:27]([CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38])[CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(=O)=O.Cl>O.CO>[C:37]([NH:36][CH2:35][CH2:34][C:11]1[CH:10]=[CH:9][CH:8]=[C:6]2[C:5]=1[CH:4]=[C:3]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]3[C:31]([CH:30]=[CH:29][CH:28]=[C:27]3[CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:33]=1)[CH:2]=[CH:7]2)(=[O:39])[CH3:38]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 70051-NaphtholHCID 5360545Sodium2×HCID 18007941HCID 18007941, compound

Product 1

HCID 9914839HCID 9914839, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 100 ml round-bottomed flask containing 30 ml of methanol, add sodium (0.07 g 0.0030 at. g.) in small portions. When the sodium has been completely used up, add naphthol (0.82 g, 3.6 mmol). Stir using a magnetic stirrer for 20 minutes. Remove the methanol by evaporation under reduced pressure. Take up the resulting residue in 15 ml of dimethylformamide. Add the compound obtained in Step C (1.2 g, 3 mmol) and heat at reflux for 12 hours. Allow the reaction mixture to cool and pour it into a mixture of 100 ml of water and 10 ml of 3M hydrochloric acid. Extract the aqueous phase twice with ethyl acetate. Wash the organic phase with an aqueous 10% sodium hydroxide solution and then with water. Dry over magnesium sulphate and remove the ethyl acetate by evaporation under reduced pressure. Recrystallise the resulting solid residue from acetonitrile.

Workup

  1. customfor 20 minutes
  2. customRemove the methanol
  3. customby evaporation under reduced pressure
  4. temperatureheat
  5. temperatureat reflux for 12 hours
  6. temperatureAllow the reaction mixture to cool
  7. additionpour it
  8. extractionExtract the aqueous phase twice with ethyl acetate
  9. washWash the organic phase with an aqueous 10% sodium hydroxide solution
  10. dry with materialDry over magnesium sulphate
  11. customremove the ethyl acetate
  12. customby evaporation under reduced pressure
  13. customRecrystallise the resulting solid residue from acetonitrile

Sources & evidence

ORD record
ord-4159b4c7d2ba4ed882bef400adcefc1d
Source dataset
uspto-grants-2001_11
Patent number
US06319930B1

Reaction notes

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