Lithium Hydroxide → 5-(4-Bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid

HRID 631909ノート

反応式

HRID 631909 の反応式
C([O:3][C:4]([C:6]1[N:7]([CH3:18])[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Li+]>C1COCC1>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[N:9]=[N:8][N:7]([CH3:18])[C:6]=2[C:4]([OH:5])=[O:3])=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 712664555-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

生成物 1

HCID 712662515-(4-Bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid収率 94.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-(4-Bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (1.2 g, 3.87 mmol) was dissolved in THF (15 mL) and lithium hydroxide solution (0.5 N, 10 mL) was added. The mixture was stirred at room temperature for 3 hrs. TLC indicated complete consumption of the starting material. The mixture was concentrated and the residue was dissolved in water (20 mL) and filtered. The filtrate was acidified with 2N hydrochloric acid (3 mL). The white solid was filtered and dried to give 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid as a white solid (1.03 g, 94.4% yield). m.p. 209-210° C.; LC-MS calcd for C10H8BrN3O2 (m/e) 283.0, obsd 284.0 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 4.26 (s, 3H), 7.66-7.72 (m, 4H), 14.20 (br s, 1H).

後処理

  1. customconsumption of the starting material
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. filtrationfiltered
  5. filtrationThe white solid was filtered
  6. customdried

出典と根拠

ORDレコード
ord-536bca20fd074e549cd650e34f873663
出典データセット
uspto-grants-2016_04
特許番号
US09321738B2

反応ノート

読み込み中…