Acetone → HCID 20382884, compound

HRID 839624Notes

Reaction equation

HRID 839624 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:17]=[CH:16][C:9]([C:10]([NH:12][CH2:13][CH2:14][OH:15])=[O:11])=[CH:8][CH:7]=1)=[O:4].[S:18]1C=CC=C1CC([O-])=O.[K+].[CH3:28][C:29](C)=[O:30]>>[C:29]([S:18][CH2:2][C:3]([NH:5][C:6]1[CH:17]=[CH:16][C:9]([C:10]([NH:12][CH2:13][CH2:14][OH:15])=[O:11])=[CH:8][CH:7]=1)=[O:4])(=[O:30])[CH3:28]

Participants

4

Reactant 3

HCID 180AcetoneHCID 203829064-(2-Chloroacetamido)-N-(2-hydroxyethyl)benzamideHCID 23696799Potassium 2-thienylacetate

Product 1

HCID 20382884HCID 20382884, compoundYield 57%

Procedure

A mixture of 4-(2-chloroacetamido)-N-(2-hydroxyethyl)benzamide (39.3 g., 0.153 mole) and potassium thiolacetate (18.3 g., 0.16 mole) in 650 ml. of acetone is heated at reflux temperature for a period of 2 hr. After standing overnight, the reaction mixture is filtered, the filtercake washed with acetone, slurried with water, filtered and the filtercake washed with water and dried to afford 34.7 g. of crude product. Crystallization of this material from ethyl acetate-methanol affords analytically pure 4-[2-(ACETYLTHIO)ACETAMIDO]N-(2-HYDROXYETHYL)BENZAMIDE, m.p. 190.0°-192.0° C. (corr.) in 57% yield.

Workup

  1. temperatureat reflux temperature for a period of 2 hr
  2. filtrationthe reaction mixture is filtered
  3. washthe filtercake washed with acetone
  4. filtrationfiltered
  5. washthe filtercake washed with water
  6. customdried
  7. customto afford 34.7 g
  8. customCrystallization of this material from ethyl acetate-methanol

Sources & evidence

ORD record
ord-7ce9b87d1e43474d8815602a67e5ba5f
Source dataset
uspto-grants-1978_06
Patent number
US04096277

Reaction notes

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