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

HRID 2413864Notes

Reaction equation

HRID 2413864 reaction equation
[NH2:1][C:2]1[C:3]([F:15])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]#[CH:13])[C:6]=2[CH:14]=1.[C:16]1(=O)[O:21][C:19](=[O:20])[C:18]2[CH2:22][CH2:23][CH2:24][CH2:25][C:17]1=2.O>C(O)(=O)C>[F:15][C:3]1[C:2]([N:1]2[C:19](=[O:20])[C:18]3[CH2:22][CH2:23][CH2:24][CH2:25][C:17]=3[C:16]2=[O:21])=[CH:14][C:6]2[N:7]([CH2:11][C:12]#[CH:13])[C:8](=[O:10])[S:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 139609955-Amino-6-fluoro-3-(prop-2-yn-1-yl)-1,3-benzothiazol-2(3H)-one

Product 1

HCID 140139642-[6-fluoro-3-(2-propynyl)-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dioneYield 18.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-6-fluoro-3-(2-propynyl)-2(3H)-benzothiazolone (0.43 g) and 3,4,5,6-tetrahydrophthalic anhydride (0.32 g) were suspended in acetic acid (5 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 was washed with water and an aqueous sodium bicarbonate solution, dried and concentrated. The residue was purified by silica gel thin layer chromatography with a mixture of ethyl acetate and hexane (1:4) to give 2-[6-fluoro-3-(2-propynyl)-2(3H)-benzothiazolon-5-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.13 g). m.p., 193°-195° C. Recrystallization from 2-propanol gave the purified product. m.p., 198°-199° C.

Workup

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

Sources & evidence

ORD record
ord-732fe8106e69447f90115be1ce9590c2
Source dataset
uspto-grants-1988_01
Patent number
US04720297

Reaction notes

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