Hydrochloric Acid → HCID 58310429, compound

HRID 716547Notes

Reaction equation

HRID 716547 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[S:6][CH:7]=[CH:8][C:2]1=2.[Cl:9][CH2:10][C:11](Cl)=[O:12].O.Cl>C(Cl)Cl>[Cl:9][CH2:10][C:11]([C:5]1[S:1][C:2]2[CH:8]=[CH:7][S:6][C:3]=2[CH:4]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6577Chloroacetyl chlorideHCID 136063Thieno(3,2-b)thiophene

Product 1

HCID 58310429HCID 58310429, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Thieno[3,2-b]-thiophene (38.5 mmol) was solubilized in anhydrous DCM (77 mL) and the chloroacetylchloride (39.66 mmol) was added. The reaction mixture was cooled down to 0° C. and A1Cl3 (43.12 mmol) solubilized in DCM (385 mL) was added slowly. The mixture was stirred at room temperature during 5 hrs. The reaction mixture was cooled again to 0° C. and water and 2N HCl were added until pH=1. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give intermediate E71 as a yellow solid in 43% yield. MS (ESI, EI+) m/z=216.8 (MH+).

Workup

  1. additionwas added slowly
  2. temperatureThe reaction mixture was cooled again to 0° C.
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. customto give intermediate E71 as a yellow solid in 43% yield

Sources & evidence

ORD record
ord-b961f60e7dc44f8d8ca03051772cdd58
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

Loading…