Potassium Iodide → 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

HRID 2039680

반응식

HRID 2039680 반응식
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].Cl.Cl[CH2:15][C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[NH2:21][C:18]1[S:19][CH:20]=[C:16]([CH2:15][O:1][N:2]2[C:10](=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:12])[N:17]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

생성물 1

HCID 3410772-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-hydroxy-1H-isoindole-1,3(2H)-dione (4.13 g, 15.0 mmol) in acetonitrile (150 mL) were added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (50.1 g, 337 mmol), cesium carbonate (210 g, 643 mmol) and potassium iodide (2.54 g, 15.3 mmol). The heterogenous mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water, the insolubles were filtered off, rinsed with water and dried over night to afford 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione as a colourless solid [36.0 g, yield 43%; HPLC/MS: m/z=276 (M+H); log P(HCOOH)=0.74].

후처리

  1. filtrationthe insolubles were filtered off
  2. washrinsed with water
  3. customdried over night

출처 및 근거

ORD 기록
ord-e2ea30608b7442e6bab564d433391754
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580799B2

연결된 노트

불러오는 중…