Acetic Anhydride → N-acetyl-3,3-dimethyl-7-nitrobenzisoselenazoline

HRID 2186755Notes

Reaction equation

HRID 2186755 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[Se:4][NH:3]1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:15]([N:3]1[C:2]([CH3:14])([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[Se:4]1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 98815673,3-Dimethyl-7-nitrobenzisoselenazoline

Product 1

HCID 22448518N-acetyl-3,3-dimethyl-7-nitrobenzisoselenazolineYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 3,3-dimethyl-7-nitrobenzisoselenazoline described in Example 1 (130 mg, 0.5 mmol) is treated with 1 ml of acetic anhydride and 1 ml of pyridine at 60° C. for 1.5 hours. The mixture is then evaporated to dryness. The residue is triturated with a mixture of ethyl acetate and cyclohexane (1:2). The red solid is filtered and rinsed to provide the expected amide (140 mg, 93%).

Workup

  1. customThe mixture is then evaporated to dryness
  2. customThe residue is triturated with a mixture of ethyl acetate and cyclohexane (1:2)
  3. filtrationThe red solid is filtered
  4. washrinsed

Sources & evidence

ORD record
ord-e652153994284b17a3324ad877bae239
Source dataset
uspto-grants-2002_06
Patent number
US06407083B1

Reaction notes

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