1,2-Dichloroethane → N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 900170노트

반응식

HRID 900170 반응식
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12](C(O)=O)=[CH:11][CH:10]=2)[O:3]1.C(Cl)CCl.[CH3:23][NH:24][CH3:25].C1C[O:29]CC1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[CH3:23][NH:24][C:25](=[O:29])[C:17]1[CH:16]=[CH:12][CH:11]=[CH:10][C:9]=1[B:4]1[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

생성물 1

HCID 69218561N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.0 g, 4.03 mmol), EDC (0.81 g, 4.23 mmol), and DMAP (catalytic amount) in 3 mL of DMF was stirred at room temperature for 1 hr, and then 2 mL of a 2M solution of N,N-dimethylamine in THF (4 mmol) was added into the reaction mixture. The resulting mixture was stirred at room temperature for 16 h. Ethyl acetate (100 mL) was added and the mixture was washed with saturated sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated. The solvent was removed to give the title compound which was used without further purification for the next step. Mass Spectrum (ESI) m/e=262 (M+1).

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 16 h
  2. washthe mixture was washed with saturated sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe solvent was removed

출처 및 근거

ORD 기록
ord-7c638b9d186d453686c94ce59c87c438
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358250B2

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