Dimethyl Sulfoxide → HCID 20352239, compound

HRID 371935Notes

Reaction equation

HRID 371935 reaction equation
[C:1]1([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]12[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:18][C:17](=O)[O:16][C:14]2=[O:15].[CH3:25]S(C)=O>O>[C:1]1([C:7]23[CH2:12][CH:11]2[CH2:10][N:9]([C:14]([C:13]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:18][C:17](=[O:16])[CH3:25])=[O:15])[CH2:8]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8359Isatoic AnhydrideHCID 101300941-Phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 20352239HCID 20352239, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7 g. of 1-phenyl-3-azabicyclo[3.1.0]hexane and 6.5 g. of isatoic anhydride in 10 ml. of dimethyl sulfoxide is warmed on a steam bath for 10 minutes. The mixture is cooled and water is added producing a gummy solid which is separated by extraction with chloroform, dried, filtered and evaporated to a dark oil. This oil is dissolved in 30 ml. of acetic anhydride, refluxed for 5 minutes, evaporated to an oil and water is added and decanted from the mixture several times. The thick oil is mixed with ethanol and a solid separates. This solid is dissolved in hot ethanol filtered and cooled giving a white solid which is recrystallized once from aqueous ethanol and once from ether to give the product as a white solid, mp 124.5°-127° C.

Workup

  1. additionA mixture of 7 g
  2. temperatureThe mixture is cooled
  3. customproducing a gummy solid which
  4. customis separated by extraction with chloroform
  5. customdried
  6. filtrationfiltered
  7. customevaporated to a dark oil
  8. dissolutionThis oil is dissolved in 30 ml
  9. temperatureof acetic anhydride, refluxed for 5 minutes
  10. customevaporated to an oil and water
  11. additionis added
  12. customdecanted from the mixture several times
  13. additionThe thick oil is mixed with ethanol
  14. dissolutionThis solid is dissolved in hot ethanol
  15. filtrationfiltered
  16. temperaturecooled
  17. customgiving a white solid which
  18. customis recrystallized once from aqueous ethanol and once from ether

Sources & evidence

ORD record
ord-aed11b6429794fb784605fa6bc26ef45
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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