Chloroacetyl chloride → HCID 12399238, compound

HRID 893269Notes

Reaction equation

HRID 893269 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12](Cl)=[O:13].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[Cl:10][CH2:11][C:12]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][C:8]#[N:9])=[CH:3][CH:4]=1)=[O:13]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8794PhenylacetonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12399238HCID 12399238, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
0 °C

Procedure

In a 1 liter round bottomed, four-necked flask with condenser, CaCl2 drying tube, pneumatic stirrer and thermometer 88.2 ml of benzylcyanide, 105.6 ml of chloroacetylchloride, and 238.2 ml of carbon disulfide are added. After the solution has been cooled to 0° C., AlCl3 is slowly added. The reaction mixture is heated to 15° C. It is subsequently stirred for another 5 minutes at +2° C., 1.2 hour at room temperature and 2 hours at 40° C. CS2 is separated and the dark oil is placed on 2.5 kg ice while stirring vigorously. The resulting brown precipitate is filtered by suction over a D4 glass filter funnel, washed with 1N hydrochloric acid, sucked quite dry, and dried in a vacuum drying oven for 18 hours at room temperature. The raw product (104.9 g) is dissolved in boiling 6.4 l i-propanol containing 34 g of activated carbon and then the product is recrystallized upon cooling. After the crystals have precipitated at room temperature, the precipitation is completed. The product is left with the mother liquor for at least 24 hours at 4° C. The white crystals are filtered by suction by means of a D4 glass filter funnel, washed with cold i-propanol and dried in a vacuum drying oven for 18 hours at room temperature.

Workup

  1. temperatureThe reaction mixture is heated to 15° C
  2. customCS2 is separated
  3. stirringwhile stirring vigorously
  4. filtrationThe resulting brown precipitate is filtered by suction over a D4 glass
  5. filtrationfilter funnel
  6. washwashed with 1N hydrochloric acid
  7. customsucked quite dry
  8. customdried in a vacuum
  9. customdrying oven for 18 hours at room temperature
  10. dissolutionThe raw product (104.9 g) is dissolved
  11. customthe product is recrystallized
  12. temperatureupon cooling
  13. customAfter the crystals have precipitated at room temperature
  14. customthe precipitation
  15. waitThe product is left with the mother liquor for at least 24 hours at 4° C
  16. filtrationThe white crystals are filtered by suction by means of a D4 glass
  17. filtrationfilter funnel
  18. washwashed with cold i-propanol
  19. customdried in a vacuum
  20. customdrying oven for 18 hours at room temperature

Sources & evidence

ORD record
ord-538c077692da4f6082a7b74065f97098
Source dataset
uspto-grants-1992_06
Patent number
US05124326

Reaction notes

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