Phenylacetyl chloride → HCID 12837866, compound

HRID 1855761Notes

Reaction equation

HRID 1855761 reaction equation
[C:1]([NH:4][C:5](=[O:8])[CH2:6][SH:7])(=[O:3])[CH3:2].[C:9]1([CH2:15][C:16](Cl)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>O>[C:1]([NH:4][C:5](=[O:8])[CH2:6][S:7][C:16](=[O:17])[CH2:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 14798Sodium HydroxideHCID 12837860HCID 12837860, compound

Product 1

HCID 12837866HCID 12837866, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One-half of the aqueous solution prepared in Step A. above was taken and ice was added while nitrogen was bubbled through the stirred solution. There was then added 4.65 g. (0.03 mole) of phenylacetyl chloride, and after that, with good stirring, there was added over 20 minutes a solution of 1.2 g. (0.03 mole) of sodium hydroxide in 30 ml. of water. Ice was added in intervals while the reaction mixture was stirred an additional hour. The water was then decanted from the solid product, after which it was triturated with cold water and decanted, then triturated with 0.5 ml. of acetic acid in 50 ml. of cold water and decanted. The solid was taken up in dichloromethane, dried, then evaporated to an oil. The oil was triturated with petroleum ether, after which it solidified, yielding 3.2 g. The product was recrystallized from dichloromethane/petroleum ether to yield 2.0 g. This material was chromatographed on a Waters high pressure liquid chromatography apparatus using silica gel and hexane: ethylacetate (2:1) as the eluent. A total of 800 mg. of product was obtained having an m.p. of 123°-124° C.

Workup

  1. additionice was added while nitrogen
  2. customwas bubbled through the stirred solution
  3. additionThere was then added 4.65 g
  4. additionIce was added in intervals while the reaction mixture
  5. customThe water was then decanted from the solid product
  6. customafter which it was triturated with cold water
  7. customdecanted
  8. customtriturated with 0.5 ml
  9. customof cold water and decanted
  10. customdried
  11. customevaporated to an oil
  12. customThe oil was triturated with petroleum ether
  13. customyielding 3.2 g
  14. customThe product was recrystallized from dichloromethane/petroleum ether
  15. customto yield 2.0 g
  16. customThis material was chromatographed on a Waters high pressure liquid chromatography apparatus
  17. customof product was obtained

Sources & evidence

ORD record
ord-9c92509bee624cec8f66e0ede51bb56e
Source dataset
uspto-grants-1980_08
Patent number
US04216160

Reaction notes

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