홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Hydrogen Bromide → 3-(2-Oxoacetyl)benzoic acid

HRID 498244
노트
인쇄 미리보기

반응식

HRID 498244 반응식
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:15]=[N:14][C:13]([CH3:16])=[N:12][CH:11]=2)[CH:5]=1.Br[CH2:19][C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26])=[O:21].Br>CS(C)=O>[C:4]([O:27][C:25](=[O:26])[CH2:24][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:15]=[N:14][C:13]([CH3:16])=[N:12][CH:11]=2)[CH:5]=1)=[O:17])([CH3:9])([CH3:5])[CH3:3].[O:2]=[CH:19][C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26])=[O:21]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 260Hydrogen BromideHCID 27568353-(Bromoacetyl)benzoic acidHCID 694894533-(3-Methyl-[1,2,4]triazin-6-yl)-benzoic acid methyl ester

생성물 2

HCID 223179033-(2-Oxoacetyl)benzoic acidHCID 694865703-[3-(3-Methyl-[1,2,4]triazin-6-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

반응 조건

온도
55 °C

실험 절차

The title compound was prepared from 3-(3-methyl-[1,2,4]triazin-6-yl)-benzoic acid methyl ester [prepared by the following procedure: To a solution of 3-bromoacetyl-benzoic acid (2.43 g, 10 mmol) in DMSO (17 ml) was added 48% aqueous HBr (3.4 ml) and the mixture was stirred at 55° C. for 0.5 h. The cooled mixture was partitioned between AcOEt and H2O, the organic layer was washed with brine, dried and evaporated in vacuum and the solid residue was triturated with Et2O/hexane to give 3-oxoacetyl-benzoic acid (1.08 g) as a white solid. A solution of this material (3.92 g, 20 mmol) and acetyl hydrazide (1.63 g, 22 mmol) in MeOH (20 ml) was stirred at RT for 1 h. The mixture was evaporated in vacuum and the residue was heated in an autoclave in 5N NH3-MeOH (30 ml) at 150° C. for 3 h. The mixture was cooled and partitionned between AcOEt and sat. NaHCO3-solution. The aqueous phase was acidified to pH 3with 3N HCl and extracted with AcOEt. The crude product obtained from the AcOEt extract was esterified by heating in 1N HCl-MeOH (80 ml) for 18 h at 50° C. and the crude ester obtained was purified by chromatography (silica gel, AcOEt) to give the methyl ester as light-yellow solid (0.45 g).] (0.8 g, 3.5 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a yellow solid (1.34 g, crude product).

후처리

  1. customprepared by the following procedure
  2. customThe cooled mixture was partitioned between AcOEt and H2O
  3. washthe organic layer was washed with brine
  4. customdried
  5. customevaporated in vacuum
  6. customthe solid residue was triturated with Et2O/hexane

출처 및 근거

ORD 기록
ord-51ccac3027534fedbf6cdec28c3a1c81
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06949542B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트