Toluene → HCID 9836930, compound

HRID 1279227Notes

Reaction equation

HRID 1279227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]([NH2:20])=O)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[O:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]([NH2:26])([CH3:25])[CH2:23]N.C1(C)C=CC=CC=1>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:9])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:20]3[CH2:21][C:22]([CH3:25])([CH3:23])[N:26]=[C:18]23)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 131282-MethylpropylenediamineHCID 12017607HCID 12017607, compound

Product 1

HCID 9836930HCID 9836930, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-1-carboxamide (25 g) (Step 1 of Example 2), 2-methyl-1,2-diaminopropane (40 mL), and toluene (125 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 slurried with ethanol. The solid was collected by filtration and dried to give the title compound (26 g) as a white solid, m.p. 168-170° C. Anal. for C19H17N2O2F: Calculated: C, 70.35; H, 5.28; N, 8.64. Found: C, 70.16; H, 5.35; N, 8.55.

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. filtrationThe solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-f3472609c1b84133a670c7fc20fb6370
Source dataset
uspto-grants-2002_09
Patent number
US06448255B1

Reaction notes

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