Hydrochloric Acid → N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide

HRID 1014391ノート

反応式

HRID 1014391 の反応式
[CH3:1][N:2]([CH3:24])[CH2:3][C:4]([N:6]([CH3:23])[C:7]1[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]([NH:13]C(=O)OC(C)(C)C)[CH:12]=1)=[O:5].Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[NH2:13][C:11]1[CH:12]=[C:7]([N:6]([CH3:23])[C:4](=[O:5])[CH2:3][N:2]([CH3:24])[CH3:1])[CH:8]=[CH:9][C:10]=1[O:21][CH3:22]

参加物

7

反応物 4

HCID 313Hydrochloric Acid2 回HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 594420081,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate

生成物 1

HCID 59441934N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide収率 84.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 1,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate (2.01 g, 5.96 mmol) in 1,4-dioxane (40 ml) was treated with 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) and stirred for 3 hours. Additional 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) was added and the reaction was stirred for 16 hours. The solution was poured into ethyl acetate, diluted with water, and neutralized by careful addition of solid potassium carbonate. The aqueous layer was washed with chloroform and the organic layers were combined, dried over sodium sulfate, filtered, and taken to a residue under reduced pressure to afford N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide (1.19 g, 5.01 mmol, 84% yield) as a tan oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.78 (d, J=8.2 Hz, 1 H), 6.48 (d, J=2.4 Hz, 1 H), 6.41 (d, J=8.2 Hz, 1 H), 4.91 (br. s., 2 H), 3.77 (s, 3 H), 3.05 (s, 3 H), 2.82 (s, 2 H), 2.12 (s, 6 H).

後処理

  1. stirringthe reaction was stirred for 16 hours
  2. washThe aqueous layer was washed with chloroform
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-c5610577d9014f6f94c291d1a2475b68
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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