Toluene → HCID 178515365, compound

HRID 889308Notes

Reaction equation

HRID 889308 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1.C([O-])(=[O:22])C.[NH4+].C1(C)C=CC=CC=1>C(O)(=O)C>[OH:22][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 59186978HCID 59186978, compound

Product 1

HCID 178515365HCID 178515365, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

50.0 mg (0.18 mmol) of the compound from Example 7 and 600 mg (7.74 mmol) ammonium acetate are heated at 180° C. as a suspension in 3 ml glacial acetic acid in a single mode microwave (Explorer from CEM) for 2 h. After a complete conversion is detected by analytical HPLC, toluene is added and the volatile components are distilled off azeotropically. The residue is taken up in water and the solid which remains is filtered off. The slightly brownish powder is subsequently washed with water and then with MTBE. After drying, 39 mg (84% of th.) of the title compound are obtained.

Workup

  1. additionis added
  2. distillationthe volatile components are distilled off azeotropically
  3. filtrationthe solid which remains is filtered off
  4. washThe slightly brownish powder is subsequently washed with water
  5. customAfter drying

Sources & evidence

ORD record
ord-a3d172ef59944ea99d5d2b3739266d5b
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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