Ethyl chloroformate → 4-Bromo-2-[(ethoxycarbonyl)amino]benzoic acid

HRID 1255513ノート

反応式

HRID 1255513 の反応式
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>C1COCC1.C1(C)C=CC=CC=1>[Br:17][C:15]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([NH:7][C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH:16]=1

参加物

5

反応物 2

HCID 10928Ethyl chloroformateHCID 886912-Amino-4-bromobenzoic acid

生成物 1

HCID 581581134-Bromo-2-[(ethoxycarbonyl)amino]benzoic acid

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

Ethyl chloroformate (5.00 ml, 52.1 mmol) was added to a solution of 2-amino-4-bromobenzoic acid (3.75 g, 17.36 mmol) in THF (70 ml) at room temperature. The mixture was heated to 70° C. and let stir for 24 hrs. The reaction was concentrated to give an oily solid. The resulting solid was diluted with toluene (50 mL), concentrated and then triturated with 5% ether/hexanes (100 mL) to give upon filtration and subsequent washing of the solid with hexane the title compound (4.6 gm, 92%) as a solid. LCMS (ES+) m/z 287.88 (M+H)+.

後処理

  1. concentrationThe reaction was concentrated
  2. customto give an oily solid
  3. concentrationconcentrated
  4. customtriturated with 5% ether/hexanes (100 mL)
  5. customto give upon filtration
  6. washsubsequent washing of the solid with hexane the title compound (4.6 gm, 92%) as a solid

出典と根拠

ORDレコード
ord-f5ae55a75eac4b78b3f42bd315477ff7
出典データセット
uspto-grants-2013_06
特許番号
US08461107B2

反応ノート

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