Hydrochloric Acid → 1-Propanone, 3-chloro-1-(5-nitrobenzo[b]thien-3-yl)-

HRID 1384843Notes

Reaction equation

HRID 1384843 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].Cl[CH:14]([CH3:18])[C:15](Cl)=[O:16].[Cl-:19].[Cl-].[Cl-].[Al+3].Cl>C(Cl)(Cl)Cl>[Cl:19][CH2:18][CH2:14][C:15]([C:10]1[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=2[S:8][CH:9]=1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1110192-Chloropropionyl chloride2×HCID 6451240Aluminum(III) Chloride2×HCID 124140845-Nitro-1-benzothiophene

Product 1

HCID 110975911-Propanone, 3-chloro-1-(5-nitrobenzo[b]thien-3-yl)-Yield 30%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1 g (5.58×10−3 moles) of 5-nitrobenzo[b]thiophene and 0.65 ml (6.64×10−3 moles) of 2-chloropropionyl chloride dissolved in 40 ml of dry chloroform was added dropwise over 650 mg of aluminum trichloride, dissolved in 20 ml dry chloroform under a nitrogen atmosphere. The mixture was left to react for 24 hours at room temperature and an additional amount of 650 mg of aluminum trichloride and 0.65 ml of 2-chloropropionyl chloride was added. After 48 hours reaction 100 ml of HCl 1.5N were added, followed by decantation and the organic phase was subsequently washed with a dilute solution of NaHCO3, with H2O and with a saturated solution of NaCl. It was dried with Na2SO4, the solvent was removed and it was purified in a silica column using hexane/toluene (25:75) as mobile phase. Yield: 30%.

Workup

  1. waitThe mixture was left
  2. customto react for 24 hours at room temperature
  3. additionwere added
  4. washthe organic phase was subsequently washed with a dilute solution of NaHCO3, with H2O and with a saturated solution of NaCl
  5. dry with materialIt was dried with Na2SO4
  6. customthe solvent was removed
  7. customit was purified in a silica column

Sources & evidence

ORD record
ord-61ce5fde7cd54fecbae65c240228c6bd
Source dataset
uspto-grants-2001_07
Patent number
US06262056B1

Reaction notes

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