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

HRID 1392259

반응식

HRID 1392259 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2c456c3544ae41e4900a48bcbda31214
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342039B2

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