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

Triethylamine → 4-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile

HRID 1436467
노트
인쇄 미리보기

반응식

HRID 1436467 반응식
C(N(CC)CC)C.[OH:8][CH2:9][C:10]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:20]=[C:21]([C:25]#[N:26])[N:22]([CH3:24])[CH:23]=2)[N:18]=1)([CH3:12])[CH3:11].Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl.O.C(OCC)(=O)C>O1CCCC1>[CH3:11][C:10]1([CH3:12])[CH2:9][O:8][C:28](=[O:30])[N:13]1[C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:20]=[C:21]([C:25]#[N:26])[N:22]([CH3:24])[CH:23]=2)[N:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 22728543Water ethylacetateHCID 866186224-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile

생성물 1

HCID 689019664-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile수율 36%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of triethylamine (0.42 mL, 3 mmol) and 4-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile (0.75 g, 2.71 mmol), prepared in the previous step, in dry tetrahydrofuran (10 mL) was added triphosgene (0.83 g, 2.8 mmol) at room temperature. After 16 h, the mixture was poured into water/ethyl acetate. The organic layer was washed with water, dried (anhydrous sodium sulfate) and evaporated. The product was purified by silica gel column chromatography (ethyl acetate:hexanes, 1:4) to afford the title compound (0.29 g, 36%) as a white powder. HRMS: calcd for C14H14N4O2S [M+H]+, 303.09102; found (ESI, [M+H]+), 303.0914; ANLC 99.6% at 210-370 nm, 9.0 min; 99.5% at 260 nm, 9.0 min, the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried (anhydrous sodium sulfate)
  3. customevaporated
  4. customThe product was purified by silica gel column chromatography (ethyl acetate:hexanes, 1:4)

출처 및 근거

ORD 기록
ord-9271670c15374ba7b85ed0ac077ec0ab
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07618990B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트