Acetic Acid → HCID 12837897, compound

HRID 1065295Notes

Reaction equation

HRID 1065295 reaction equation
C(N(CC)CC)C.[S:8]1C=CC=C1CC(O)=O.CN(C)C=O.[C:22]([NH:25][C:26](=[O:35])[CH:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:24])[CH3:23].[C:36]([OH:39])(=O)[CH3:37]>>[C:22]([NH:25][C:26](=[O:35])[CH:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[S:8][C:36](=[O:39])[CH3:37])(=[O:24])[CH3:23]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6228Dimethylformamide2×HCID 8471Triethylamine2×HCID 159702-Thiopheneacetic acid2×HCID 12837905HCID 12837905, compound

Product 1

HCID 12837897HCID 12837897, compound

Procedure

The triethylamine salt of thiolacetic acid was made by adding 2.23 g. (0.022 mole) of triethylamine to a stirred and ice-cooled solution of 1.67 g. (0.022 mole) of thiolacetic acid in 15 ml. of dimethylformamide. This solution was in turn added dropwise with stirring and ice-cooling to a solution of 4.2 g. (0.02 mole) of the compound prepared in Step B. above in 15 ml. of dimethylformamide, while maintaining the temperature below 10° C. The reaction mixture was stirred an additional hour, and then there was added 1 ml. of acetic acid. The reaction mixture was poured onto ice and a thick yellow oil formed. The mixture was decanted, and the ice was washed with water and again decanted. The yellow oil was taken up in 75 ml. of ether, dried, and evaporated, leaving 2.5 g. of yellow oil. This was chromatographed on a Waters high pressure liquid chromatography apparatus using 25% ethylacetate in hexane as the eluent. A water-white oil weighing 1.9 g. was obtained. A seed was formed by rubbing a little with petroleum ether and the bulk of material precipitated quickly to yield 1.6 g. of material having an m.p. of 96° C.

Workup

  1. additionby adding 2.23 g
  2. temperatureice-cooled solution of 1.67 g
  3. additionadded dropwise
  4. temperatureice-cooling to a solution of 4.2 g
  5. stirringThe reaction mixture was stirred an additional hour
  6. additionthere was added 1 ml
  7. additionThe reaction mixture was poured onto ice
  8. customa thick yellow oil formed
  9. customThe mixture was decanted
  10. washthe ice was washed with water
  11. customagain decanted
  12. dry with materialof ether, dried
  13. customevaporated
  14. customleaving 2.5 g
  15. customThis was chromatographed on a Waters high pressure liquid chromatography apparatus
  16. customwas obtained
  17. customA seed was formed
  18. customthe bulk of material precipitated quickly
  19. customto yield 1.6 g

Sources & evidence

ORD record
ord-38e4b58d58c74d97bab51b4a65208afa
Source dataset
uspto-grants-1982_05
Patent number
US04329363

Reaction notes

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