Dichloromethane → HCID 71245552, compound

HRID 575497Notes

Reaction equation

HRID 575497 reaction equation
C(O[CH:4](OCC)[CH2:5][S:6][C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:28][CH3:29])=[C:12]([S:19][CH2:20][CH:21](OCC)OCC)[CH:13]=2)[CH:8]=1)C.ClC1C=CC=CC=1.ClCCl>CO>[CH3:29][O:28][C:11]1[C:12]2[S:19][CH:20]=[CH:21][C:13]=2[C:14]2[CH:15]=[C:16]([O:17][CH3:18])[C:7]3[S:6][CH:5]=[CH:4][C:8]=3[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7964ChlorobenzeneHCID 866765302,6-Bis-(2,2-diethoxy-ethylsulfanyl)-3,7-dimethoxy-naphthalene

Product 1

HCID 71245552HCID 71245552, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

Compound 6 (5.0 g, 10.3 mmol) and 6.8 g of 84% polyphorphoric acid were added into a 250 mL 3-neck flask equipped with a condenser. The system was flashed with argon for 15 minutes before 50 mL of anhydrous chlorobenzene was added. The mixture was heated at 140° C. for 40 hours before it was cooled down to room temperature. Dichloromethane (100 mL) was added. The organic mixture was washed with saturated NaHCO3 before the solvent was removed under vacuum. Methanol (100 mL) was added before compound 7 (2.0 g, ˜66% yield) was collected as a white solid by filtration, washed with methanol and dried in vacuo. 1H NMR (CDCl3, 500 MHz): δ 7.97 (d, 2H, J=5.5 Hz), δ 7.62 (d, 2H, J=5.5 Hz), 67.51 (s, 2H), δ 4.18 (s, 6H).

Workup

  1. customequipped with a condenser
  2. additionwas added
  3. temperaturewas cooled down to room temperature
  4. washThe organic mixture was washed with saturated NaHCO3 before the solvent
  5. customwas removed under vacuum

Sources & evidence

ORD record
ord-3af71bcf06de461e9661449fafd65b21
Source dataset
uspto-grants-2015_05
Patent number
US09035004B2

Reaction notes

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