1,4-Dioxane → (3,5-Diaminophenyl)[4-(phenylethynyl)phenyl]methanone

HRID 2294667Notes

Reaction equation

HRID 2294667 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([N+:26]([O-])=O)[CH:25]=1)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)=[O:8])([O-])=O.O1CCOCC1>Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([NH2:26])[CH:25]=1)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 21475482HCID 21475482, compound

Product 1

HCID 18433932(3,5-Diaminophenyl)[4-(phenylethynyl)phenyl]methanoneYield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a 1 L Erlenmeyer flask equipped with a magnetic stirrer was charged 3,5-dinitro-4'-phenylethynylbenzophenone (19.6 g, 0.053 mol) and 1,4-dioxane (450 mL). The orange solution was cooled to ~10°-15° C. by means of an ice bath. A cooled solution (~10° C.) of stannous chloride dihydrate (78.4 g, 0.35 mol) in concentrated hydrochloric acid (300 mL) was added dropwise while maintaining the temperature between 10°-20° C. After the addition, the ice bath was removed and the reaction mixture allowed to warm to room temperature. The mixture was stirred at room temperature for ~16 h. During this time the product precipitated from solution. The solid was collected, placed in distilled water and neutralized with aqueous ammonium hydroxide. The crude material was collected by filtration, washed in water and dried at 65° C. for 1 h in flowing air to afford 16.0 g (98%) of a crude solid. The crude product was recrystallized form toluene to afford 13.1 g (80%) of a yellow powder, mp (DSC, 10° C./min) 156° C. Anal. calcd. for C21H16N2O: C, 80.74%; H, 5.16%; N, 8.97%; Found: C, 80.73%; H, 5.10%; N 8.98%.

Workup

  1. customTo a 1 L Erlenmeyer flask equipped with a magnetic stirrer
  2. temperatureThe orange solution was cooled to ~10°-15° C. by means of an ice bath
  3. temperaturewhile maintaining the temperature between 10°-20° C
  4. additionAfter the addition
  5. customthe ice bath was removed
  6. customDuring this time the product precipitated from solution
  7. customThe solid was collected
  8. filtrationThe crude material was collected by filtration
  9. washwashed in water
  10. customdried at 65° C. for 1 h
  11. customto afford 16.0 g (98%) of a crude solid
  12. customThe crude product was recrystallized form toluene

Sources & evidence

ORD record
ord-d5a4788bd5a041899325cd1dfc9aae16
Source dataset
uspto-grants-1997_11
Patent number
US05689004

Reaction notes

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