Toluene → HCID 9879582, compound

HRID 1279224Notes

Reaction equation

HRID 1279224 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:11]([NH2:13])=O)[O:3]1.[CH3:20][C:21](N)([CH3:24])[CH2:22][NH2:23].C1(C)C=CC=CC=1>O>[OH:3][C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2](=[O:1])[N:23]2[CH2:22][C:21]([CH3:24])([CH3:20])[N:13]=[C:11]12

Participants

5

Reactant 3

HCID 1140TolueneHCID 131282-MethylpropylenediamineHCID 2334123-oxo-1-phenyl-1,3-dihydro-2-benzofuran-1-carboxamide

Product 1

HCID 9879582HCID 9879582, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-oxo-1-phenyl-1,3-dihydro-2-benzofuran-1-carboxamide (10 g), 2-methyl-1,2-diaminopropane (15 mL), and toluene (100 mL) was heated at reflux for 18 h in a flask equipped with a water separator. The mixture was cooled to ambient temperature and extracted with water. The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ethanol to give the title compound (57.3 g), m.p. 186-188° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h in a flask
  3. extractionextracted with water
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-13d49954cb0c45ccaa8a6d7b73975aa7
Source dataset
uspto-grants-2002_09
Patent number
US06448255B1

Reaction notes

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