3,4,5,6-Tetrahydrophthalic anhydride → 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2(3H)-benzothiazolone

HRID 1199615노트

반응식

HRID 1199615 반응식
[NH2:1][C:2]1[C:3]([F:19])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]3[N:16]=[C:15]([CH3:17])[O:14][N:13]=3)[C:6]=2[CH:18]=1.[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2[CH2:26][CH2:27][CH2:28][CH2:29][C:21]1=2>C(O)(=O)C>[F:19][C:3]1[C:2]([N:1]2[C:23](=[O:24])[C:22]3[CH2:26][CH2:27][CH2:28][CH2:29][C:21]=3[C:20]2=[O:25])=[CH:18][C:6]2[N:7]([CH2:11][C:12]3[N:16]=[C:15]([CH3:17])[O:14][N:13]=3)[C:8](=[O:10])[S:9][C:5]=2[CH:4]=1

참가 물질

4

반응물 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 199794815-amino-6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone

생성물 1

HCID 199794756-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2(3H)-benzothiazolone수율 70%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 5-amino-6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone (2.8 g) and acetic acid (20 ml) was admixed with 3,4,5,6-tetrahydrophthalic anhydride (1.6 g), stirred at a temperature of 20° to 30° C. for 30 minutes, and then heated under refluxing for 2 hours. The reaction mixture was distilled under a reduced pressure to remove the acetic acid therefrom, and the residue was worked up by chromatography, wherein a silica gel column was used together with an eluant. comprising a tetrahydrofuran/toluene mixture (a 1:3 mixture), so that the aimed compound, i.e. 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-5-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2(3H)-benzothiazolone (2.9 g) was obtained. m.p. 198°-199° C.

후처리

  1. temperatureheated
  2. temperatureunder refluxing for 2 hours
  3. distillationThe reaction mixture was distilled under a reduced pressure
  4. customto remove the acetic acid

출처 및 근거

ORD 기록
ord-4e7cd7cc79ff4d5b96083cee4a289642
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902335

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