Trifluoroacetic acid → 3-(Octadecyloxy)-5-(phenylmethoxy)benzenamine

HRID 1110284ノート

反応式

HRID 1110284 の反応式
CC(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:10]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:9]=1)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:23]([O:22][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 193890303-(Octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester

生成物 1

HCID 193889513-(Octadecyloxy)-5-(phenylmethoxy)benzenamine収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 28 g of 3-(octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester and 76 ml of trifluoroacetic acid in 700 ml of methylene chloride was kept at room temperature for 2 hours. The solution was concentrated at reduced pressure and the residue was extracted with methylene chloride. The extract was washed with NaHCO3 solution, dried and concentrated to a solid which was dissolved in 1000 ml of ether. The solution was treated with 21 ml of 3N HCl in ethanol. The hydrochloride salt which precipitated was filtered and treated with excess NaHCO3 to liberate the free base which was extracted with methylene chloride. The dried extract was concentrated at reduced pressure to give 20.4 g (89% yield, mp 57°-59°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzenamine.

後処理

  1. concentrationThe solution was concentrated at reduced pressure
  2. extractionthe residue was extracted with methylene chloride
  3. washThe extract was washed with NaHCO3 solution
  4. customdried
  5. concentrationconcentrated to a solid which
  6. dissolutionwas dissolved in 1000 ml of ether
  7. additionThe solution was treated with 21 ml of 3N HCl in ethanol
  8. customThe hydrochloride salt which precipitated
  9. filtrationwas filtered
  10. additiontreated with excess NaHCO3
  11. extractionwas extracted with methylene chloride
  12. extractionThe dried extract
  13. concentrationwas concentrated at reduced pressure

出典と根拠

ORDレコード
ord-1201da6a907b44afb7aa864a82f20c31
出典データセット
uspto-grants-1994_06
特許番号
US05324747

反応ノート

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