Dimethyl Sulfoxide → 2-(N-Benzyl-N-(2-Hydroxyethyl)Amino)-2-(4-Fluorophenyl)Acetamide

HRID 1094533Notes

Reaction equation

HRID 1094533 reaction equation
[CH2:1]([N:8]([CH:12]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:13]#[N:14])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=[O:24]>>[CH2:1]([N:8]([CH:12]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:13]([NH2:14])=[O:24])[CH2:9][CH2:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 9838744[Benzyl(2-hydroxyethyl)amino](4-fluorophenyl)acetonitrile

Product 1

HCID 582329202-(N-Benzyl-N-(2-Hydroxyethyl)Amino)-2-(4-Fluorophenyl)Acetamide

Procedure

5 g of [Benzyl-(2-hydroxyethyl)-amino]-(4-fluorophenyl)-acetonitrile of Formula XI and 15 ml of dimethylsulfoxide (DMSO) were charged in a clean and dry 4 neck round bottom flask followed by stirring for about 20 minutes. 3.8 g. of potassium carbonate was charged to the above reaction solution followed by addition of 7 ml of 50% hydrogen peroxide over about 30 minutes. The resultant reaction solution was stirred for about 2 hours, after completion of the reaction, reaction was quenched by adding 50 ml of water over about 30 minutes. The reaction suspension was stirred for about 1 hour. Separated solid was filtered and the solid was washed with 10 ml of water. Wet cake obtained and 50 ml of petroleum ether were charged in a clean and dry 4neck round bottom flask followed by stirring for about 15 minutes. The solid was filtered and the solid was dried at about 30° C. for about 5 hours to yield 3.8 g of the title compound.

Workup

  1. customdry 4 neck round bottom flask
  2. additionof potassium carbonate was charged to the above reaction solution
  3. additionfollowed by addition of 7 ml of 50% hydrogen peroxide over about 30 minutes
  4. customThe resultant reaction solution
  5. stirringwas stirred for about 2 hours
  6. customafter completion of the reaction, reaction
  7. customwas quenched
  8. additionby adding 50 ml of water over about 30 minutes
  9. stirringThe reaction suspension was stirred for about 1 hour
  10. customSeparated solid
  11. filtrationwas filtered
  12. washthe solid was washed with 10 ml of water
  13. customWet cake obtained
  14. customdry
  15. customround bottom flask followed
  16. stirringby stirring for about 15 minutes
  17. filtrationThe solid was filtered
  18. customthe solid was dried at about 30° C. for about 5 hours

Sources & evidence

ORD record
ord-8a81af35c8d0411b9f2fda784a90b03c
Source dataset
uspto-grants-2012_03
Patent number
US08133994B2

Reaction notes

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