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

HRID 477595

Reaction equation

HRID 477595 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-6315777bab0346709ccb5beb232dceb4
Source dataset
uspto-grants-1989_12
Patent number
US04888428

Linked notes

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