Acetic Anhydride → 1-Amino-2-naphthalenethiol

HRID 2427820Notes

Reaction equation

HRID 2427820 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1O.C(O[S:26]([O-])(=O)=O)CCCCCCCCCCC.[Na+].C(OC(=O)C)(=O)C>O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[SH:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 145351-Amino-2-naphtholHCID 3423265Sodium Lauryl Sulfate

Product 1

HCID 1133141-Amino-2-naphthalenethiolYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 mmol of 1-aminonaphthalene-2-ol was added to 20 mL of water, and 20 mg of sodium dodecylsulfate was added while agitating to obtain a uniform mixture. 7.5 mmol of acetic anhydride was added for 5 minutes. An acetylated product was precipitated in in 5-10 minutes. The precipitation product was filtrated and rinsed with 1 ml of water twice followed by drying under vacuum. A non-precipitated reaction mixture was extracted with 25 ml of ethyl acetate twice. The separated organic layer was dried with anhydrous sodium sulfate, and a solvent was removed using a rotatary evaporator under a reduced pressure to obtain 1-aminonaphthalene-2-thiol at a yield of 73%.

Workup

  1. additionwas added
  2. customto obtain a uniform mixture
  3. customAn acetylated product was precipitated in in 5-10 minutes
  4. filtrationThe precipitation product was filtrated
  5. washrinsed with 1 ml of water
  6. customby drying under vacuum
  7. extractionA non-precipitated reaction mixture was extracted with 25 ml of ethyl acetate twice
  8. dry with materialThe separated organic layer was dried with anhydrous sodium sulfate
  9. customa solvent was removed
  10. customa rotatary evaporator under a reduced pressure

Sources & evidence

ORD record
ord-67cb42ab285f47feaa19e3083698696a
Source dataset
uspto-grants-2011_06
Patent number
US07968715B2

Reaction notes

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