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

HRID 1914613

반응식

HRID 1914613 반응식
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Cl[CH2:14][C:15]1[N:16]=[C:17]([NH2:20])[S:18][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[NH2:20][C:17]1[S:18][CH:19]=[C:15]([CH2:14][O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[N:16]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 10796Cesium carbonateHCID 732294-Chloromethylthiazol-2-ylamine

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A suspension of N-hydroxyphthalimide (50.0 g, 306 mmol), 4-(chloromethyl)-1,3-thiazol-2-amine (50.1 g, 337 mmol), cesium carbonate (210 g, 0.64 mol) and potassium iodide (2.54 g, 15.3 mmol) in acetonitrile (440 mL) was stirred at room temperature for 18 h. Water (300 mL) was added, the precipitate was filtered off and washed with water until colourless, then dried in vacuo overnight to afford 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione as a colourless solid [36.0 g; 43% of theory; HPLC/MS: m/z=276 (M+H); log P(HCOOH)=0.74].

후처리

  1. filtrationthe precipitate was filtered off
  2. washwashed with water until colourless,
  3. customthen dried in vacuo overnight

출처 및 근거

ORD 기록
ord-386cc9bab711421ead518e0e0c58ee48
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614217B2

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