Triethylamine → 4-chloro-N-(methoxycarbonylmethylthio)acetylanthranilic acid methyl ester

HRID 1781624ノート

反応式

HRID 1781624 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=1)[NH2:6].C(N(CC)CC)C.[CH3:20][O:21][C:22](=[O:29])[CH2:23][S:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=1)[NH:6][C:26](=[O:27])[CH2:25][S:24][CH2:23][C:22]([O:21][CH3:20])=[O:29]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 80001Methyl 4-chloroanthranilateHCID 12361281Methyl [(2-chloro-2-oxoethyl)sulfanyl]acetate

生成物 1

HCID 223647744-chloro-N-(methoxycarbonylmethylthio)acetylanthranilic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

21.24 g (0.114 mol) of 4-chloroanthranilic acid methyl ester and 19.1 ml (0.137 mol) of triethylamine are placed in 180 ml of methylene chloride at 0°. A solution of 20.9 g (0.114 mol) of 2-(chloroformylmethylthio)-acetic acid methyl ester (T. Terasawa and T. Okada, J. Org. Chem., 42, 1163 (1977)) in 20 ml of methylene chloride is added dropwise thereto and the mixture is then stirred for 15 minutes at 0° and for 3 hours at room temperature. The reaction mixture is extracted with water and brine and the aqueous phases are washed with methylene chloride. The organic phases are combined, dried with sodium sulfate, filtered and concentrated. Chromatography of the crude product on silica gel with hexane/ethyl acetate (4:1) yields, in the form of yellowish crystals, 4-chloro-N-(methoxycarbonylmethylthio)acetylanthranilic acid methyl ester which is still impure.

後処理

  1. extractionThe reaction mixture is extracted with water and brine
  2. washthe aqueous phases are washed with methylene chloride
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-3c74e80b8099436f9d73ec980f6d944a
出典データセット
uspto-grants-1997_05
特許番号
US05633379

反応ノート

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