Sodium Hydroxide → 4-{benzyl[(2-chloro-1,3-thiazol-5-yl)methyl]amino}furan-2(5H)-one

HRID 451340

반응식

HRID 451340 반응식
[CH2:1]([NH:8][C:9]1[CH2:13][O:12][C:11](=[O:14])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:17][C:18]1[S:19][C:20]([CH2:23]Cl)=[CH:21][N:22]=1>C(COC)OC>[CH2:1]([N:8]([CH2:23][C:20]1[S:19][C:18]([Cl:17])=[N:22][CH:21]=1)[C:9]1[CH2:13][O:12][C:11](=[O:14])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 27631792-Chloro-5-chloromethylthiazoleHCID 134024534-(benzylamino)furan-2(5H)-one

생성물 1

HCID 684891974-{benzyl[(2-chloro-1,3-thiazol-5-yl)methyl]amino}furan-2(5H)-one수율 71%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
50 °C

실험 절차

6.3 g of 4-(benzylamino)furan-2(5H)-one (Example 16) are initially charged in 75 ml of dimethoxyethane at room temperature. Subsequently, 1.3 g of sodium hydroxide are added and, at 40° C., 34.4 g of a 15% solution of 2-chloro-5-(chloromethyl)-1,3-thiazole in dimethoxyethane are metered in. The mixture is stirred at 50° C. for a further 6 h. The solvent is substantially removed under reduced pressure and the residue is admixed with 50 ml of water and 50 ml of methylene chloride. The organic phase is removed, and the aqueous phase is extracted once again with 50 ml of methylene chloride. The combined methylene chloride phases are dried over sodium sulphate and the solvent is removed under reduced pressure. 6.9 g of 4-{benzyl[(2-chloro-1,3-thiazol-5-yl)methyl]amino}furan-2(5H)-one are obtained (this corresponds to 71% yield).

후처리

  1. customThe solvent is substantially removed under reduced pressure
  2. customThe organic phase is removed
  3. extractionthe aqueous phase is extracted once again with 50 ml of methylene chloride
  4. dry with materialThe combined methylene chloride phases are dried over sodium sulphate
  5. customthe solvent is removed under reduced pressure

출처 및 근거

ORD 기록
ord-21a7e2cd56fd4ac88c4bb560daf0bd29
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487112B2

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