Triethylamine → HCID 59441965、化合物

HRID 1014223ノート

反応式

HRID 1014223 の反応式
[CH3:1][C:2]1[CH:7]=[C:6](N)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C([N:14](CC)CC)C.CN(C1C=CC=CN=1)C.Cl.[CH3:29][N:30]([CH2:32][C:33](Cl)=[O:34])[CH3:31].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:29][N:30]([CH3:31])[CH2:32][C:33]([NH:14][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:34]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 118984-Nitro-m-toluidineHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride2 回

生成物 1

HCID 59441965HCID 59441965、化合物収率 91.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-methyl-4-amino nitro benzene (5.00 g, 32.3 mmol) in dichloromethane (200 mL) was added triethylamine (12 mL, 97 mmol, 3 equiv.), dimethylaminopyridine (ca 500 mg) and dimethylaminoacetyl chloride hydrochloride (6.50 g, 41.1 mmol, 1.25 equiv.). The resulting clear solution was stirred 24 hours, at which time additional dimethylaminoacetyl chloride hydrochloride (1.50 g, 9.5 mmol, 0.30 equiv.) was added. After an additional 24 hrs. the reaction was poured into saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (0 to 10% methonal/CH2CL2) to give N2,N2-dimethyl-N1-(4-methyl-3-nitrophenyl)glycinamide (7.0 g, 29.5 mmol, 91% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.40 (s, 6 H), 2.55 (s, 3 H), 3.11 (s, 2 H), 7.28 (d, J=8.42 Hz, 1H), 7.86 (dd, J=8.32, 2.29 Hz, 1 H), 8.15 (d, J=2.38 Hz, 1 H), 9.33 (s, 1 H),

後処理

  1. additionwas added
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. custompurified by chromatography on SiO2 (0 to 10% methonal/CH2CL2)

出典と根拠

ORDレコード
ord-e861a87f926e4ea2946b7466bf462726
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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