Thioglycolic Acid → 5-(3,5-Dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-2-methylbenzoic acid

HRID 488715

反応式

HRID 488715 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:16](=[O:17])[NH:15][C:14](=[O:18])[C:13](C(O)=O)=[N:12]2)[CH:7]=[CH:8][C:9]=1[CH3:10])([OH:3])=[O:2].[OH-].[Na+].SCC(O)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[O:17]=[C:16]1[NH:15][C:14](=[O:18])[CH:13]=[N:12][N:11]1[C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]([CH:5]=1)[C:1]([OH:3])=[O:2]

参加物

7

反応物 3

HCID 1133Thioglycolic AcidHCID 14798Sodium Hydroxide2 回HCID 22267498HCID 22267498、化合物

生成物 1

HCID 222674555-(3,5-Dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-2-methylbenzoic acid収率 73.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
102.5 °C

実験手順

2-(3-Carboxy-4-methyl-phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (110 gm) was added to 8 volumes of water with 2.4 equivalents of sodium hydroxide and 1.1 equivalents of mercaptoacetic acid. The reaction mixture was heated to reflux (100-105° C.) for approximately 18 hours at which point the reaction was complete by HPLC. 30% Sodium hydroxide and toluene were added and the resulting mixture was stirred. Upon settling a large interface was noted. More water, toluene and some ethyl acetate were added. The interface was minimized. The water layer was separated and treated with 2N HCl. At pH 2 solids precipitated out and the slurry was cooled to <10° C. The solids were filtered off in a slow filtration and dried in a vacuum oven to give 69 gm of the title compound.

後処理

  1. temperatureThe reaction mixture was heated
  2. customThe water layer was separated
  3. additiontreated with 2N HCl
  4. customAt pH 2 solids precipitated out
  5. temperaturethe slurry was cooled to <10° C
  6. filtrationThe solids were filtered off in a slow filtration
  7. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-741d88600b7c44df86c5a10630f14134
出典データセット
uspto-grants-2005_12
特許番号
US06974812B2

関連ノート

読み込み中…