Toluene → HCID 18770593, compound

HRID 479527Notes

Reaction equation

HRID 479527 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1.[O-]S([O-])(=O)=O.[Mg+2].[C:26]1([CH3:36])[CH:31]=[CH:30]C(S(O)(=O)=O)=[CH:28][CH:27]=1.[C:37]1(C)C=CC=CC=1>>[N:11]1([CH:30]([NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:31][C:26]([CH3:36])([CH3:37])[CH:27]=[CH2:28])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1

Participants

6

Reactant 5

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 120844-ChlorobenzamideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 178418385HCID 178418385, compound

Product 1

HCID 18770593HCID 18770593, compound

Procedure

A suspension of 4-chlorobenzamide (1.32 g, 8.5 mmol), Example 92A (0.96 g, 8.5 mmol), benzotriazole (1.01 g, 8.5 mmol), and MgSO4 (2.00 g, 16.6 mmol) in toluene (50 mL) was treated with p-toluenesulfonic acid (100 mg, 0.53 mmol). The solution was heated at reflux for 48 hours, cooled to ambient temperature, filtered and concentrated to dryness. The crude material was purified by recrystallization from EtOAc/hexanes to provide 1.301 g of the desired product as a white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 48 hours
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified by recrystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-64c2274d504648b48e7991f166e24592
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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