Triethylamine → 4-Nitro-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

HRID 29673

反応式

HRID 29673 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[NH2:13].C(N(CC)CC)C.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[NH:13][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][C:25]([O:24][C:23]([F:22])([F:34])[F:35])=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 596476Methyl 4-nitroanthranilate

生成物 1

HCID 692054354-Nitro-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-amino-4-nitro-benzoic acid methyl ester (5.00 g, 25.5 mmol) in methylene chloride (75 mL) was added triethylamine (4.13 g, 40.8 mmol) followed by 4-trifluoromethoxy-benzoyl chloride (6.87 g, 30.6 mmol). This mixture was allowed to stir overnight at ambient temperature. The mixture was filtered, partitioned against brine, the layers were separated, and the aqueous layer was extracted with one portion of ethyl acetate. The organics were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was recrystallized from ethyl acetate (250 mL) to give 4-nitro-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (6.83 g, 70%) as pale-yellow crystals. 1H NMR (500 MHz, DMSO-d6); δ 11.53 (s, 1H), 9.20 (d, 1H), 8.19 (d, 1H), 8.10 (d, 2H), 8.07 (dd, 1H), 7.63 (d, 2H), 3.91 (s, 3H).

後処理

  1. filtrationThe mixture was filtered
  2. custompartitioned against brine
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with one portion of ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was recrystallized from ethyl acetate (250 mL)

出典と根拠

ORDレコード
ord-4a04ac522eff4b92bea5eced178dcb90
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

関連ノート

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