Nitric Acid → 2-Acetamido-5-nitroresorcinol ditosylate

HRID 647223Notes

Reaction equation

HRID 647223 reaction equation
[S:1]([O:11][C:12]1[CH:28]=[CH:27][CH:26]=[C:14]([O:15][S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:13]=1[NH:29][C:30](=[O:32])[CH3:31])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N+:33]([O-])([OH:35])=[O:34].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[S:1]([O:11][C:12]1[CH:28]=[C:27]([N+:33]([O-:35])=[O:34])[CH:26]=[C:14]([O:15][S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:13]=1[NH:29][C:30](=[O:32])[CH3:31])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 1118Sulfuric AcidHCID 714103112-Acetamidoresorcinol ditosylate

Product 1

HCID 714103122-Acetamido-5-nitroresorcinol ditosylateYield 76.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

A solution of 2-acetamidoresorcinol ditosylate (11.9 g, 0.025 mole) in acetic anhydride (75 ml) was cooled to below 15° C. Meanwhile, nitric acid (1.9 ml, 0.029 mole) was slowly added to cold acetic anhydride (20 ml) with stirring so that the temperature did not exceed 25° C. The nitric acid solution was then added to the cold acetanalide solution. Finally, the sulfuric acid (0.75 ml) was added. The mixture was stirred an additional six hours, during which time the reaction temperature rose to 30° C. The mixture was pured into ice water (1500 ml) and stirred one hour. The resulting precipitate was collected, air dried, and recrystalllized from isopropyl alcohol (100 ml) to yield a tan crystallline solid (9.9 g, 76.0 percent). TLC showed the product to be pure.

Workup

  1. customdid not exceed 25° C
  2. stirringThe mixture was stirred an additional six hours, during which time the reaction temperature
  3. customrose to 30° C
  4. stirringstirred one hour
  5. customThe resulting precipitate was collected
  6. customair dried

Sources & evidence

ORD record
ord-35294aad0c624c16a06115e298e63114
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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