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Acetic Anhydride → HCID 54339084、化合物

HRID 1633430
ノート
印刷プレビュー

反応式

HRID 1633430 の反応式
CN=[C:3]([OH:19])[C:4]1[C:5](=[C:9]([N+]([O-])=O)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:28]=[C:29]([SH:34])[CH:30]=[CH:31][C:32]=1[Cl:33].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([S:34][C:9]2[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=[C:4]3[C:3]([O:7][C:6](=[O:8])[C:5]=23)=[O:19])[CH:30]=[CH:31][C:32]=1[Cl:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 799643,4-DichlorobenzenethiolHCID 178485491HCID 178485491、化合物

生成物 1

HCID 54339084HCID 54339084、化合物

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒
HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

18.84 g (75 mmols) of 3,5-dinitrophthalic acid N-methylimide [prepared according to Example 2] are initially introduced into 250 ml of ethyl acetate and treated with 30.4 g (220 mmols) of ground, anhydrous potassium carbonate, and 14 g (78 mmols) of 3,4-dichlorothiophenol are then added dropwise. After the addition of 95 ml of tetrahydrofuran, the mixture is stirred overnight and then evaporated to dryness. The residue is kept under reflux overnight in 100 ml of water, the mixture is extracted at 25° C. with petroleum ether and filtered and the aqueous filtrate is acidified with 300 ml of 2N HCl and heated under reflux. After 2.5 hours, the mixture is cooled and extracted with tetrahydrofuran/toluene and the extract is washed with saturated NaCl solution, dried over sodium sulfate and evaporated. The residue is warmed to the reflux temperature with 100 ml of toluene and 7.66 g (75 mmols) of acetic anhydride and, after cooling, the mixture is evaporated. After recrystallisation from methylene chloride/n-pentane, 22.2 g (80% of theory) of 3-(3,4-dichlorophenylthio)-5-nitrophthalic anhydride are obtained; melting point: 154°-7° C.

後処理

  1. additionare then added dropwise
  2. customevaporated to dryness
  3. temperatureunder reflux overnight in 100 ml of water
  4. extractionthe mixture is extracted at 25° C. with petroleum ether
  5. filtrationfiltered
  6. temperatureheated
  7. temperatureunder reflux
  8. waitAfter 2.5 hours
  9. temperaturethe mixture is cooled
  10. extractionextracted with tetrahydrofuran/toluene
  11. washthe extract is washed with saturated NaCl solution
  12. dry with materialdried over sodium sulfate
  13. customevaporated
  14. temperatureafter cooling
  15. customthe mixture is evaporated
  16. customAfter recrystallisation from methylene chloride/n-pentane, 22.2 g (80% of theory) of 3-(3,4-dichlorophenylthio)-5-nitrophthalic anhydride
  17. customare obtained

出典と根拠

ORDレコード
ord-101bb549327b425b8e4e3c9482b8cd1c
出典データセット
uspto-grants-1984_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04480105

反応ノート

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