Dimethylformamide → N-[2-t-Butyl-5-(6-cyclohexyl-5-oxohexyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 977826ノート

反応式

HRID 977826 の反応式
C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH:12]1[C:25]2[CH:24]([CH2:26][C:27](O)=[O:28])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.[C:30]([C:34]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][C:45](=[O:53])[CH2:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)=[CH:37][C:35]=1[NH2:36])([CH3:33])([CH3:32])[CH3:31]>C(OCC)C.N1C=CC=CC=1.C(Cl)Cl>[C:30]([C:34]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][C:45](=[O:53])[CH2:46][CH:47]2[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]2)=[CH:37][C:35]=1[NH:36][C:27](=[O:28])[CH2:26][CH:24]1[C:25]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[O:17][C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:33])([CH3:31])[CH3:32]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 8346622-(9H-xanthen-9-yl)acetic acidHCID 199662372-t-Butyl-5-(6-cyclohexyl-5-oxohexyl)aniline

生成物 1

HCID 19966079N-[2-t-Butyl-5-(6-cyclohexyl-5-oxohexyl)phenyl]-2-(9H-xanthen-9-yl)acetamide収率 86.4%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

0.66 ml (7.65 mmol) of oxalyl chloride and 30 mg of N,N-dimethylformamide were added, in turn, to 10 ml of a methylene chloride suspension containing 368 mg (1.53 mmol) of 2-(9H-xanthen-9-yl)acetic acid. The suspension was stirred in an ice bath for 30 minutes and then at room temperature for 1 hour. At the end of this time, the solvent and excess reagents, were removed by distillation under reduced pressure. The residue was again dissolved in 10 ml of methylene chloride, and the resulting solution was placed in an ice bath. 2 ml of a methylene chloride solution containing 458 mg (1.39 mmol) of 2-t-butyl-5-(6-cyclohexyl-5-oxohexyl)aniline and 0.56 ml of pyridine were then added to the solution, and the mixture was stirred for 10 minutes. The reaction solution was then diluted with diethyl ether, washed with a dilute aqueous solution of sodium hydroxide, with dilute aqueous hydrochloric acid and with water, in that order. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 40 g of silica gel. Elution with a 100:20 by volume mixture of hexane and ethyl acetate afforded 663 mg (yield 86%) of the title compound as crystals, melting at 126°-127° C. (after recrystallization from a mixture of diethyl ether and hexane).

後処理

  1. waitat room temperature for 1 hour
  2. customAt the end of this time, the solvent and excess reagents, were removed by distillation under reduced pressure
  3. dissolutionThe residue was again dissolved in 10 ml of methylene chloride
  4. customthe resulting solution was placed in an ice bath
  5. additionwere then added to the solution
  6. stirringthe mixture was stirred for 10 minutes
  7. washwashed with a dilute aqueous solution of sodium hydroxide, with dilute aqueous hydrochloric acid and with water, in that order
  8. customThe solvent was then removed by distillation under reduced pressure
  9. washElution with a 100:20
  10. additionby volume mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-c5d3df44ceb84049ae41788535f95d1f
出典データセット
uspto-grants-1997_03
特許番号
US05614550

反応ノート

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