Hydrochloric Acid → HCID 20405640, compound

HRID 2164438Notes

Reaction equation

HRID 2164438 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=1)=[CH:8][CH:9]=[C:10]2[OH:15])(=[O:3])[CH3:2].Cl.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].C(O)C>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)=[CH:8][CH:9]=[C:10]2[OH:15])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 20405638HCID 20405638, compound

Product 1

HCID 20405640HCID 20405640, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

5-Acetamido-4-(3-nitrophenylthio)-1-naphthol (1.0 g), iron pin dust (3.0 g), ethanol (25 ml) and concentrated hydrochloric acid (0.05 ml) were stirred and heated under reflux for 24 hours. Sodium carbonate (0.1 g) was heated to the hot mixture which was then filtered through keiselguhr. The filtrate was concentrated to dryness by rotary evaporation. The solid was stirred with a little ethanol and insoluble material was filtered off (0.2 g). The ethanol filtrate was diluted with water to give another 0.55 g of product. Total yield 0.75 g (82%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. filtrationwas then filtered through keiselguhr
  4. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  5. filtrationwas filtered off (0.2 g)
  6. additionThe ethanol filtrate was diluted with water

Sources & evidence

ORD record
ord-4532cc63dec24dd89e397a5941344c85
Source dataset
uspto-grants-1985_03
Patent number
US04504568

Reaction notes

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