Hydrochloric Acid → Acetamide, N-(2-anthracenyl)-

HRID 1682503Notes

Reaction equation

HRID 1682503 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].Cl>O1CCCC1.C(=S)=S>[C:16]([NH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1)(=[O:18])[CH3:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 119372-AminoanthraceneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 96865Acetamide, N-(2-anthracenyl)-Yield 97%

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Acetamidoanthracene was prepared in 97% yield by stirring a solution of 1 equivalent of 2-aminoanthracene and 1.5 equivalents of acetic anhydride in dry tetrahydrofuran for 3 hours at room temperature. This product (2.9 g) was dissolved in 35 ml of carbon disulfide and 4 ml of oxalyl chloride was added. The stirred mixture was cooled to 0° C. and treated with 2.5 g of anhydrous aluminum chloride. Another 35 ml of carbon disulfide and 2.5 g of aluminum chloride were added after 2 hours. The mixture was stirred 2 hours at 0° C. and overnight at room temperature and then treated with dilute HCl. The brown precipitate that formed was washed with water and then digested well with 5% NaOH solution. After collection, the insoluble solids were washed with water and dried in air to give 1.25 g (35%) of a mixture of 2-,6-, and 7-acetamido-1,9-oxalylanthracenes.

Workup

  1. customThe brown precipitate that formed
  2. washwas washed with water
  3. customAfter collection
  4. washthe insoluble solids were washed with water
  5. customdried in air

Sources & evidence

ORD record
ord-8456b1d59c56493f8acb307006438918
Source dataset
uspto-grants-1997_06
Patent number
US05635506

Reaction notes

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