Hydrochloric Acid → HCID 458355, compound

HRID 1089184Notes

Reaction equation

HRID 1089184 reaction equation
[CH3:1][C:2]([C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)=[O:3].[Cl-].[Al+3].[Cl-].[Cl-].[C:21](Cl)(=[O:23])[CH3:22].Cl>C(=S)=S>[C:21]([C:12]1[CH:13]=[CH:14][C:9]2[S:8][C:7]3[CH:15]=[CH:16][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=3[C:10]=2[CH:11]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 3120271-(Dibenzo[b,d]thiophen-2-yl)ethan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 458355HCID 458355, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 45.3 g of 2-dibenzothienyl methyl ketone in one liter of carbon disulfide was added 106 g of anhydrous aluminum chloride. To this was added 17.3 g of acetyl chloride over 8 minutes. This mixture was refluxed for 3 hours and then poured into a mixture of 2 liters of crushed ice and 400 ml of concentrated hydrochloride acid. This mixture was stirred until the green color had changed to pale tan, then the solid was collected washed with water and air dried. This solid was collected, washed with water and air dried. This solid was dissolved in 2 liters of hot acetontride, filtered, concentrated to about one liter and allowed to crystallize, giving 39.0 g of the desired product as tan crystals, mp 207°-210° C.

Workup

  1. temperatureThis mixture was refluxed for 3 hours
  2. customthe solid was collected
  3. washwashed with water and air
  4. customdried
  5. customThis solid was collected
  6. washwashed with water and air
  7. customdried
  8. dissolutionThis solid was dissolved in 2 liters of hot acetontride
  9. filtrationfiltered
  10. concentrationconcentrated to about one liter
  11. customto crystallize

Sources & evidence

ORD record
ord-999d060c6e3842b0b4d4cd0bf99f358c
Source dataset
uspto-grants-1990_10
Patent number
US04965284

Reaction notes

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