Triethylamine → 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamide

HRID 393835

反応式

HRID 393835 の反応式
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[C:13]([C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[C:20](O)=[O:21])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:30][C:27]([C:24]1[CH:23]=[C:19]([CH:18]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:25]=1[OH:26])[C:20]([NH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:12][CH:11]=1)=[O:21])([CH3:28])[CH3:29]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 112524674-Nitrobenzylamine hydrochloride

生成物 1

HCID 219185543,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(4-nitrophenyl)methyl]-benzamide収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1.88 g (10 mmoles) of p-nitrobenzylamine hydrochloride, 2.5 g (10 mmoles) of 3,5-di-tert-butyl-4-hydroxybenzoic acid, 1.38 ml (10 mmoles) of triethylamine and 2.26 g (11 mmoles) of dicyclohexylcarbodiimide are introduced into a 250 ml flask containing 25 ml of THF. The reaction medium is agitated for 15 hours at ambient temperature, the precipitate which appears is filtered out and rinsed with the minimum quantity of ethyl acetate. After concentration of the solution under reduced pressure, the residue is precipitated from a mixture of ethyl acetate/diethyl ether (1/4) and filtered. The crystals are washed abundantly with diethyl ether in order to finally produce, after drying, a white powder with a yield of 74% (2.85 g). Melting point: 230-231° C.

後処理

  1. filtrationthe precipitate which appears is filtered out
  2. washrinsed with the minimum quantity of ethyl acetate
  3. customAfter concentration of the solution under reduced pressure, the residue is precipitated from a mixture of ethyl acetate/diethyl ether (1/4)
  4. filtrationfiltered
  5. washThe crystals are washed abundantly with diethyl ether in order
  6. customto finally produce
  7. customafter drying

出典と根拠

ORDレコード
ord-99cb7217f35e4e9e8b18f6221e7d6561
出典データセット
uspto-grants-2004_10
特許番号
US06809088B2

関連ノート

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