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

HRID 2946
ノート
印刷プレビュー

反応式

HRID 2946 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 6547Azobisisobutyronitrile2 回HCID 543041065-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-(ethylmethylamino)-2-thioxo-4-thiazolidinone

生成物 1

HCID 538291925-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-(ethylmethylamino)-4-thiazolidinone収率 29.8%

試薬・触媒・溶媒 4

HCID 1140Toluene溶媒HCID 6212Chloroform溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

7.02 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]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.

後処理

  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

出典と根拠

ORDレコード
ord-95854aeecbe74885a11782806e4adc91
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05731336

反応ノート

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