Sulfuric Acid → 5-Benzoyl-2-nitrobenzamide

HRID 2247890Notes

Reaction equation

HRID 2247890 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([CH:16]=1)[C:14]#[N:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:21]>O>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([CH:16]=1)[C:14]([NH2:15])=[O:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10586886HCID 10586886, compound

Product 1

HCID 198160645-Benzoyl-2-nitrobenzamideYield 54.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.9 parts of intermediate 13, namely 5-benzoyl-2-nitrobenzonitrile, 166 parts of sulfuric acid and 10 parts of water was heated at 90° C. for 13/4 hours. The reaction mixture was poured into ice-water. The precipitate was filtered off and recrystallized from methanol. The product was filtered off, washed with methanol and 2,2'-oxybispropane and dried in vacuo at 60°-70° C., yielding 5.23 parts (54.8%) of 5-benzoyl-2-nitrobenzamide; mp. 244.3° C. (intermediate 14).

Workup

  1. filtrationThe precipitate was filtered off
  2. customrecrystallized from methanol
  3. filtrationThe product was filtered off
  4. washwashed with methanol and 2,2'-oxybispropane
  5. customdried in vacuo at 60°-70° C.

Sources & evidence

ORD record
ord-32825c8ba8fc4b67bd2f52de3025fcbe
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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