Hydrochloric Acid → HCID 86673529, compound

HRID 1424563Notes

Reaction equation

HRID 1424563 reaction equation
Cl[Sn]Cl.[N+:4]([C:7]1[CH:8]=[C:9]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:10]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1)([O-])=O.Cl>C1COCC1>[C:15]1([C:14]#[C:13][C:11]2[CH:12]=[C:7]([CH:8]=[C:9]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:10]=2)[NH2:4])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 70974553HCID 70974553, compound

Product 1

HCID 86673529HCID 86673529, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of SnCl2 (0.96 g, 5.10 mmol) was added slowly (1 h) to the mixture of ((5-nitro-1,3-phenylene)bis(ethyne-2,1-diyl))dibenzene (0.33 g, 1.02 mmol) and HCl (1 mL) in THF (10 mL). The reaction mixture was stirred at room temperature for 3 hours. After neutralization with NaOH (1.0 N solution), the product was extracted with EtOAc and dried over (Na2SO4). Solvent was evaporated to afford 0.26 g (86%) of the product: 1H-NMR (400 MHz, CDCl3) δ 7.51 (m, 4H), 7.34 (m, 6H), 7.14 (t, J=1.3 Hz, 1H), 6.82 (d, J=1.3 Hz, 2H).

Workup

  1. extractionAfter neutralization with NaOH (1.0 N solution), the product was extracted with EtOAc
  2. dry with materialdried over (Na2SO4)
  3. customSolvent was evaporated

Sources & evidence

ORD record
ord-06ffea88f4af412884f340b4f3ab0d7a
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

Loading…