Triethylamine → N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)oxalamide

HRID 906239ノート

反応式

HRID 906239 の反応式
Cl[C:2](=[O:8])[C:3](OCC)=[O:4].[NH2:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])=[C:12]([CH3:22])[CH:11]=1.CCN(CC)CC.[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH2:33][NH2:34]>C1COCC1.CCOC(C)=O>[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH2:33][NH:34][C:2](=[O:8])[C:3]([NH:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])=[C:12]([CH3:22])[CH:11]=1)=[O:4]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 575405781-(4-Amino-2-methylphenoxy)-2-methylpropan-2-ol

生成物 1

HCID 57540557N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)oxalamide収率 98.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Slow addition of a solution of ethyl 2-chloro-2-oxoacetate (4.69 g, 34.4 mmol) in THF (30 ml) to a solution of 1-(4-amino-2-methylphenoxy)-2-methylpropan-2-ol (6.10 g, 31.2 mmol) in THF (100 mL) resulted in formation of a precipitate as the reaction stirred at RT for 30 min. At which time a solution of Et3N (13.06 mL, 94 mmol) and 2,2-dimethoxyethanamine (3.94 g, 37.5 mmol) in EtOAc (100 mL) was added prior to heating the mixture at reflux for 25 hours. After cooling and concentration under vacuum, the residue, following dilution with CH2Cl2, was extracted with aqueous 0.5 N HCl (2×150 ml). The CH2Cl2 layer was dried over sodium sulfate and concentrated to yield N1-(2,2-dimethoxyethyl)-N2-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)-oxalamide (11.40 g, 30.6 mmol, 98% yield) as white solid which was carried forward without further purification.

後処理

  1. customresulted in formation of a precipitate as the reaction
  2. temperatureto heating the mixture
  3. temperatureat reflux for 25 hours
  4. temperatureAfter cooling
  5. concentrationconcentration under vacuum
  6. extractionwas extracted with aqueous 0.5 N HCl (2×150 ml)
  7. dry with materialThe CH2Cl2 layer was dried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-db3170a291f94157851b6a3d7b348187
出典データセット
uspto-grants-2011_09
特許番号
US08012984B2

反応ノート

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