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

HRID 900170ノート

反応式

HRID 900170 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7c638b9d186d453686c94ce59c87c438
出典データセット
uspto-grants-2008_04
特許番号
US07358250B2

反応ノート

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