1,2-Dichloroethane → N-methyl-N-methoxy-3-(2-pyridyl)-phenylacetamide

HRID 840740ノート

反応式

HRID 840740 の反応式
Cl.[CH3:2][O:3][NH:4][CH3:5].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:30]=[C:31]([CH2:35][C:36](O)=[O:37])[CH:32]=[CH:33][CH:34]=1.C(Cl)CCl.C([O-])(O)=O.[Na+]>CN(C=O)C.[Cl-].[Na+].O.CCOC(C)=O>[CH3:5][N:4]([O:3][CH3:2])[C:36](=[O:37])[CH2:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)[CH:30]=1

参加物

10

反応物 6

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 120760552-(3-(Pyridin-2-yl)phenyl)acetic acid

生成物 1

HCID 22620144N-methyl-N-methoxy-3-(2-pyridyl)-phenylacetamide収率 88.8%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of N-methoxy-N-methylamine hydrochloride (0.980 g, 10.0 mmol) in DMF (25 mL) was added N-methylmorpholine (1.21 mL, 11.0 mmol), HOBt (1.50 g, 11.1 mmol), 3-(2-pyridyl)-phenylacetic acid (2.36 g, 11.1 mmol), and EDC (2.13 g, 11.1 mmol). The reaction was stirred overnight whereupon it was poured into a rapidly-stirred mixture of 150 mL each of EtOAc, 10% NaHCO3, and brine. After stirring for 30 min, the layers were separated and the aqueous layer was washed with fresh EtOAc (150 mL). The combined organic layers were washed with 10% Na2CO3, and brine, then dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, 3:1 EtOAc:hexane) gave 2.275 g of the title compound: MS (ES+) (MH+) 257.2.

後処理

  1. stirringAfter stirring for 30 min
  2. customthe layers were separated
  3. washthe aqueous layer was washed with fresh EtOAc (150 mL)
  4. washThe combined organic layers were washed with 10% Na2CO3, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0b0aebf3f1ed4b7d99ba05a81fad5c8f
出典データセット
uspto-grants-2002_04
特許番号
US06369077B1

反応ノート

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