Triethylamine → 2-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester

HRID 1392259

反応式

HRID 1392259 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[NH2:6].C(N(CC)CC)C.[C:22]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=1[NH:6][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([C:22]([CH3:24])([CH3:23])[CH3:25])=[CH:27][CH:28]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 596476Methyl 4-nitroanthranilate

生成物 1

HCID 691945292-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester収率 86%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 4-nitro-anthranilic acid methyl ester (5.060 g, 25.8 mmol) in CH2Cl2 (200 mL) was added triethylamine (8 mL) and 4-tert-butyl benzoyl chloride and the reaction was stirred overnight at rt. It was then poured into brine, extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 2-(4-tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester (1.841 g, 86%) as a yellow solid. mp=146.0-148.4° C.; mass spectrum (−ES, M−H) m/z 355. 1H NMR (400 MHz, DMSO-d6); δ 11.60 (bs, 1H), 9.35 (d, 1H), 8.20 (d, 1H), 8.02 (dd, 1H), 7.90 (d, 2H), 7.64 (d, 2H), 3.95 (s, 3H), 1.36 (s, 9H). Elemental analysis: Calcd. for C19H20N2O5: C, 64.04; H, 5.66; N, 7.86. Found: C, 64.04; H, 5.79; N, 7.76.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-2c456c3544ae41e4900a48bcbda31214
出典データセット
uspto-grants-2008_03
特許番号
US07342039B2

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