Toluene → HCID 9883158, compound

HRID 1279229Notes

Reaction equation

HRID 1279229 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.[NH2:21][CH2:22][CH:23](N)[CH3:24].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:21]3[CH2:22][C@@H:23]([CH3:24])[N:20]=[C:18]23)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6567PropylenediamineHCID 12017607HCID 12017607, compound

Product 1

HCID 9883158HCID 9883158, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-1-carboxamide (12.5 g) (Step 1 of Example 2), 1,2-diaminopropane (13.5 g), and toluene (150 mL) was heated at reflux for 18 h in a flask equipped with a water separator. The mixture was evaporated to dryness. The residue was treated with hot ethanol (200 mL). The insoluble material was collected by filtration and dried to give the title compound (4.3 g) as a white solid m.p. 229-232° C. Mass spectrum (EI, M+) m/z 310. 1H NMR (400 MHz, DMSO-d6) δ 8.04 (d, 1H), 7.62 (t, 1H), 7.51 (t, 1H), 7.33 (m, 3H), 7.10 (t, 2H), 7.04 (s, 1H), 4.13 (m, 1H), 4.02 (dd, 1H), 3.52 (dd, 1H), and 1.20 ppm (d, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h in a flask
  3. customThe mixture was evaporated to dryness
  4. additionThe residue was treated with hot ethanol (200 mL)
  5. filtrationThe insoluble material was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-888b65e7436649eeab75db64867468db
Source dataset
uspto-grants-2002_09
Patent number
US06448255B1

Reaction notes

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