N,O-Dimethylhydroxylamine → 3-cyano-N,4-dimethoxy-N-methylbenzamide

HRID 655450

反応式

HRID 655450 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O)#[N:2].CN([C:17]([O:21][N:22]1N=NC2C=CC=N[C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CONC>C(Cl)Cl.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([N:22]([O:21][CH3:17])[CH3:23])=[O:8])#[N:2]

参加物

6

反応物 3

HCID 14232N,O-DimethylhydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 219909723-Cyano-4-methoxybenzoic acid

生成物 1

HCID 593547633-cyano-N,4-dimethoxy-N-methylbenzamide収率 105.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 3-cyano-4-methoxybenzoic acid (1.0 g, 5.60 mmol) in DCM (30 mL) were added HATU (3.20 g, 8.01 mmol), N-methoxy,N-methylamine (0.82 g, 8.01 mmol) and TEA (2.3 mL, 17.01 mmol) at RT under a nitrogen atmosphere. The reaction mixture was then stirred at RT for 2 h, diluted with water and the aqueous layer was extracted with DCM (3×50 mL). The combined organic extracts were washed with water (50 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford 3-cyano-N,4-dimethoxy-N-methylbenzamide (1.3 g, 100%) as a white solid.

後処理

  1. extractionthe aqueous layer was extracted with DCM (3×50 mL)
  2. washThe combined organic extracts were washed with water (50 mL) and brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-2e953f56177f4ba3a1f52f03baa08ecb
出典データセット
uspto-grants-2011_12
特許番号
US08071595B2

関連ノート

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