Dimethyl Sulfoxide → HCID 12680125, compound

HRID 1855725Notes

Reaction equation

HRID 1855725 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.CS(C)=O.[NH2:17][C:18]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][S:20][CH:19]=1>O>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:17][C:18]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][S:20][CH:19]=1)=[O:4]

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8359Isatoic AnhydrideHCID 12520022HCID 12520022, compound

Product 1

HCID 12680125HCID 12680125, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.4 g. of isatoic anhydride, 22 ml. of dimethylsulfoxide and some ground glass is stirred and put in an oil bath at 120° C. A mixture of 12.6 g. of 3-amino-4-ethoxythiophene in 17 ml. of dimethylsulfoxide is added dropwise over 30 minutes at 120°-129° C. The mixture is heated at 125°-129° C. for one hour, cooled, poured into ice and water and extracted with dichloromethane. The extract is dried over magnesium sulfate, filtered and evaporated to an oil. This oil is dissolved in methanol, filtered, cooled and a few drops of water are added. The solid is removed by filtration and the filtrate is evaporated to an oil. This oil is dissolved in methanol, a few drops of water are added and the mixture is chilled overnight. The solid is collected by filtration giving o-amino-N-(4-ethoxy-3-thienyl)-benzamide.

Workup

  1. additionA mixture of 14.4 g
  2. customput in an oil bath at 120° C
  3. additionA mixture of 12.6 g
  4. temperatureThe mixture is heated at 125°-129° C. for one hour
  5. temperaturecooled
  6. extractionextracted with dichloromethane
  7. dry with materialThe extract is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to an oil
  10. dissolutionThis oil is dissolved in methanol
  11. filtrationfiltered
  12. temperaturecooled
  13. additiona few drops of water are added
  14. customThe solid is removed by filtration
  15. customthe filtrate is evaporated to an oil
  16. dissolutionThis oil is dissolved in methanol
  17. additiona few drops of water are added
  18. temperaturethe mixture is chilled overnight
  19. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-f6151ed4079b4c74b82c7d65e3104c86
Source dataset
uspto-grants-1980_08
Patent number
US04216148

Reaction notes

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