Ethanol → HCID 14274201, compound

HRID 1032003Notes

Reaction equation

HRID 1032003 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[C:11]2[OH:16])(=[O:4])=[O:3].C(O)C.[N:20]([O-])=[O:21].[Na+]>O.[Cl-].[Zn+2].[Cl-]>[N:20]([C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][CH:14]=[CH:15][C:6]=2[NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:11]=1[OH:16])=[O:21]

Participants

6

Reactant 3

HCID 702EthanolHCID 104704Methanesulfonamide, N-(5-hydroxy-1-naphthalenyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 14274201HCID 14274201, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture comprising 119 g of 5-methanesulfonylamino-1-naphthol, 100 g of zinc chloride and 500 ml of ethanol was heated at 50° C., and then a solution of 35 g of sodium nitrite as dissolved in 70 ml of water was added dropwise thereto at 50° to 65° C. After being heated and stirred at 60° to 65° C. for 2 hours, the resulting solution was cooled with water to room temperature, and reddish brown crystals formed were taken out by filtration and washed with ethanol. The crystals were added to 200 ml of concentrated hydrochloric acid and stirred for 1 hour at room temperature, and then 200 ml of water was added thereto. Yellowish brown crystals (2-nitroso-5-methanesulfonylamino-1-naphthol) formed were taken out by filtration, washed with water and dried. Yield: 90 g.

Workup

  1. additionwas added dropwise
  2. customat 50° to 65° C
  3. temperatureAfter being heated
  4. customformed
  5. filtrationwere taken out by filtration
  6. washwashed with ethanol
  7. additionThe crystals were added to 200 ml of concentrated hydrochloric acid
  8. stirringstirred for 1 hour at room temperature
  9. addition200 ml of water was added

Sources & evidence

ORD record
ord-9abec76542314cb5849ae40ff6f0558d
Source dataset
uspto-grants-1990_09
Patent number
US04956456

Reaction notes

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