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

HRID 840740노트

반응식

HRID 840740 반응식
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

참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b0aebf3f1ed4b7d99ba05a81fad5c8f
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369077B1

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