Chlorosuccinimide → 1H-Pyrrole-2-carboxylic acid, 4-chloro-3,5-dimethyl, ethyl ester

HRID 1874999노트

반응식

HRID 1874999 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Cl:13]N1C(=O)CCC1=O>CN(C=O)C>[Cl:13][C:6]1[C:2]([CH3:1])=[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH:4][C:5]=1[CH3:7]

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester

생성물 1

HCID 1435841H-Pyrrole-2-carboxylic acid, 4-chloro-3,5-dimethyl, ethyl ester수율 29%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (0.100 g, 0.598 mmol) in DMF (2 ml) was added N-chlorosuccinimide (0.120 g, 0.897 mmol). The reaction mixture was stirred at RT for 4 h. The solvent was evaporated and purification by column chromatography (hexanes/EtOAc) afforded ethyl 4-chloro-3,5-dimethyl-1H-pyrrole-2-carboxylate (0.035 g, 29%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.68 (br. s., 1H) 4.22 (q, 2H) 2.19 (s, 3H) 2.15 (s, 3H) 1.28 (t, 3H). MS: m/z 202.3 (M+1).

후처리

  1. customThe solvent was evaporated
  2. custompurification by column chromatography (hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-f7b0ae033fb74b33a02805cd14482c56
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

반응 노트

불러오는 중…