Toluene → HCID 9946396, compound

HRID 1279228Notes

Reaction equation

HRID 1279228 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][C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]1N.C1(C)C=CC=CC=1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:9])[C:12]3[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10](=[O:17])[N:21]3[CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]4[N:20]=[C:18]23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 438061,2-Diaminocyclohexane, trans-HCID 12017607HCID 12017607, compound

Product 1

HCID 9946396HCID 9946396, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-1-carboxamide (5 g) (Step 1 of Example 2), trans 1,2-diaminocyclohexane (8.3 g), and toluene (75 mL) was heated at reflux for 66 h in a flask equipped with a water separator. The mixture was evaporated to dryness and the residual gum was extracted with hexane. The residue was chromatographed over silica gel and eluted with 10% methanol in methylene. Crystallization from ethyl acetate afforded the title compound (2.7 g) as a white solid m.p. 203-205° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 66 h in a flask
  3. customThe mixture was evaporated to dryness
  4. extractionthe residual gum was extracted with hexane
  5. customThe residue was chromatographed over silica gel
  6. washeluted with 10% methanol in methylene
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-97edcc2a865941cdb72f40deefd1c68c
Source dataset
uspto-grants-2002_09
Patent number
US06448255B1

Reaction notes

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