Water → 2-[3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolon-5-yl]4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

HRID 477595

반응식

HRID 477595 반응식
[NH2:1][C:2]1[C:3]([F:18])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=2[CH:17]=1.[C:19]1(=O)[O:24][C:22](=[O:23])[C:21]2[CH2:25][CH2:26][CH2:27][CH2:28][C:20]1=2.O>C(O)(=O)C>[CH2:15]([O:14][C:12]([CH2:11][N:7]1[C:6]2[CH:17]=[C:2]([N:1]3[C:22](=[O:23])[C:21]4[CH2:25][CH2:26][CH2:27][CH2:28][C:20]=4[C:19]3=[O:24])[C:3]([F:18])=[CH:4][C:5]=2[S:9][C:8]1=[O:10])=[O:13])[CH3:16]

참가 물질

5

반응물 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 140142455-amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolone

생성물 1

HCID 140142462-[3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolon-5-yl]4,5,6,7-tetrahydro-2H-isoindole-1,3-dione수율 19.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

5-Amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)benzothiazolone (140 mg) and 3,4,5,6-tetrahydrophthalic anhydride (90 mg) were suspended in acetic acid (3 ml), and the resultant suspension was heated under reflux for 5 hours. After being allowed to cool, water was added thereto, and the resultant mixture was extracted with ethyl acetate. The extract ws washed with water and sodium bicarbonte solution, dried and concentrated. The residue was purified by silica gel thin layer chromatography with a mixture of ethyl acetate and hexane (1:2) to give 2-[3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolon-5-yl]4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (40 mg). m.p., 155.5°-156.5° C.

후처리

  1. temperatureunder reflux for 5 hours
  2. temperatureto cool
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. washThe extract ws washed with water and sodium bicarbonte solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel thin layer chromatography with a mixture of ethyl acetate and hexane (1:2)

출처 및 근거

ORD 기록
ord-6315777bab0346709ccb5beb232dceb4
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04888428

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