Diethyl Ether → HCID 12837902, compound

HRID 1855767Notes

Reaction equation

HRID 1855767 reaction equation
[C:1]([S:4][CH2:5][C:6]([NH2:8])=[O: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.CCOCC>S(=O)(=O)(O)O.CCCCCC>[C:9]1([CH2:15][C:16]([NH:8][C:6](=[O:7])[CH2:5][S:4][C:1](=[O:3])[CH3:2])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7679Phenylacetyl chlorideHCID 51082772-(Acetylthio)acetamide

Product 1

HCID 12837902HCID 12837902, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8058HexaneSolvent

Procedure

A reaction mixture comprising 6.65 g. (0.05 mole) of 2-(acetylthio)acetamide, 10 ml. of 2-phenylacetyl chloride, and 1 drop of sulfuric acid was heated in a steam bath for 0.5 hour, and then allowed to stand overnight at room temperature, after which it solidified. There was then added 50 ml. of ether and 20 ml. of hexane, followed by stirring for 10 minutes and then filtering. A yield of 8.5 g. of a tan solid was obtained, which was then chromatographed on 100 g. of silica gel, eluting with 5% ether in dichloromethane, followed by concentration to dryness. The solid was suspended in 60 ml. of ethanol and stirred in an ice bath for 1 hour. The product of white crystals, m.p. 153°-155° C., was obtained in a 5.6 g. yield.

Workup

  1. additionThere was then added 50 ml
  2. filtrationfiltering
  3. customof a tan solid was obtained
  4. customwhich was then chromatographed on 100 g
  5. washof silica gel, eluting with 5% ether in dichloromethane
  6. concentrationfollowed by concentration to dryness
  7. stirringof ethanol and stirred in an ice bath for 1 hour
  8. customThe product of white crystals, m.p. 153°-155° C., was obtained in a 5.6 g
  9. customyield

Sources & evidence

ORD record
ord-82908aee71f149ad99658928b8def460
Source dataset
uspto-grants-1980_08
Patent number
US04216160

Reaction notes

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