Hydrochloric Acid → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-(ethylmethylamino)-4-thiazolidinone

HRID 467197

반응식

HRID 467197 반응식
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=S)[N:19]([N:23]([CH2:25][CH3:26])[CH3:24])[C:18]2=[O:27])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C.Cl>C(Cl)(Cl)Cl.CCCCCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][N:19]([N:23]([CH2:25][CH3:26])[CH3:24])[C:18]2=[O:27])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 6547Azobisisobutyronitrile2회HCID 543041065-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-(ethylmethylamino)-2-thioxo-4-thiazolidinone

생성물 1

HCID 538291925-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-(ethylmethylamino)-4-thiazolidinone

시약·촉매·용매 4

HCID 1140Toluene용매HCID 6212Chloroform용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

7.02 g of 5-[[3,5-bis(1,1-dimethylethyl)-4hydroxyphenyl]methylene-3-(ethylmethylamino)-2-thioxo-4-thiazolidinone (from Example 40D) and 86.3 ml of toluene were stirred and heated to 60° C. under a nitrogen atmosphere. To this was added 18.6 ml of tri-n-butyl tin hydride and 0.43 g of AIBN. The resultant mixture was heated to reflux temperature for 30 minutes. At that time an additional 0.43 g of AIBN was added. The resultant mixture was heated at reflux temperature for an additional 30 minutes, cooled and transferred to a separatory funnel. To this was added 100 ml of 1N hydrochloric acid and 100 ml of ethyl acetate. The resultant mixture was shaken and separated. The organic layer was washed with brine, dried over sodium sulfate, filtered, evaporated and subsequently chased with chloroform to give an orange/red oil which was taken up in 50 ml of chloroform and filtered. The filtrate was chromatographed on a silica gel column using an 8000 ml gradient of 10-40% ethyl acetate in hexane. Those fractions identified as containing product were evaporated and chased with chloroform. To these fractions were added 15 ml of hexane and the resultant solution was heated slightly. A precipitate formed which was diluted to about 25 ml with additional hexane. The resultant mixture was triturated for about 2 hours, filtered and then washed with hexane to yield 1.94 g of the desired product, m.p. 133.5-135° C.

후처리

  1. temperatureto reflux temperature for 30 minutes
  2. temperatureat reflux temperature for an additional 30 minutes
  3. temperaturecooled
  4. customtransferred to a separatory funnel
  5. customseparated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give an orange/red oil which
  11. filtrationfiltered
  12. customThe filtrate was chromatographed on a silica gel column
  13. additionas containing product
  14. customwere evaporated
  15. additionTo these fractions were added 15 ml of hexane
  16. temperaturethe resultant solution was heated slightly
  17. customA precipitate formed which
  18. customThe resultant mixture was triturated for about 2 hours
  19. filtrationfiltered
  20. washwashed with hexane

출처 및 근거

ORD 기록
ord-7695691aa67d4ef794f18cbe0a059524
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05158966

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