Sodium Hydroxide → 2-Amino-1-naphthalenethiol

HRID 1906401Notes

Reaction equation

HRID 1906401 reaction equation
[OH-].[Na+].NC1[S:5][C:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH:10]=[CH:9][C:7]=2[N:8]=1>O.C(O)CO>[NH2:8][C:7]1[CH:9]=[CH:10][C:11]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:6]=1[SH:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 838513Naphtho[2,1-d]thiazol-2-ylamine

Product 1

HCID 122815222-Amino-1-naphthalenethiol

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 30.0 g sodium hydroxide in 30 mL of water and 140 mL of ethylene glycol was added 18.0 g of 2-aminobenzo[g]benzothiazole. The mixture was heated at reflux under nitrogen for 20 hours and diluted with 80 mL of water. After cooling, the mixture was filtered, then the filtrate was chilled in an ice-bath and neutralized with acetic acid. The aqueous suspension was extracted with ether (3×200 mL) and the combined extracts were dried (magnesium sulfate). Removal of the solvent gave the product to which heptane (3×150 mL) was added and the solvent was removed under reduced pressure. (This step removed traces of acetic acid). The yield of the 2-aminonaphthalene-1-thiol was 15.4 g (97%), mp 108°-110°. A sample of this compound was recrystallized from ethanol, mp 109°-110°. This compound is sensitive to air and therefore was used immediately in the next step of the synthetic scheme.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 20 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. temperaturethe filtrate was chilled in an ice-bath
  6. extractionThe aqueous suspension was extracted with ether (3×200 mL)
  7. dry with materialthe combined extracts were dried (magnesium sulfate)
  8. customRemoval of the solvent
  9. customgave the product to which heptane (3×150 mL)
  10. additionwas added
  11. customthe solvent was removed under reduced pressure
  12. custom(This step removed traces of acetic acid)
  13. customA sample of this compound was recrystallized from ethanol, mp 109°-110°

Sources & evidence

ORD record
ord-ef90eb5d59f147dca65f104d18e540d6
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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