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

HRID 488715

반응식

HRID 488715 반응식
[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]

참가 물질

7

반응물 3

HCID 1133Thioglycolic AcidHCID 14798Sodium Hydroxide2회HCID 22267498HCID 22267498, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매2회HCID 1140Toluene용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
102.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-741d88600b7c44df86c5a10630f14134
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974812B2

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