Sodium Carbonate → 6-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-3H-benzooxazol-2-one

HRID 1935390Notes

Reaction equation

HRID 1935390 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:2]1.Br[CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]2[NH:23][C:24](=[O:26])[O:25][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C(C)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:22]4[NH:23][C:24](=[O:26])[O:25][C:21]=4[CH:20]=3)[CH2:14][CH2:15]2)=[N:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 133060876-Bromoethylbenzoxazolone

Product 1

HCID 108098036-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-3H-benzooxazol-2-one

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser were added 4.82 grams (0.022 mol) of N-(3-benzisothiazolyl)piperazine (prepared according to the procedure given in U.S. Pat. No. 4,411,901), 5.32 grams (0.022 mol) of 6-(2-bromoethyl)benzoxazolone, 2.33 grams (0.022 mol) of sodium carbonate, and 50 ml of methyl isobutyl ketone. The mixture was refluxed for 18 hours. The reaction was cooled and partitioned between ethyl acetate and water. The ethyl acetate layer was isolated, washed with water and saturated aqueous sodium chloride solution dried over sodium sulfate, and evaporated to an oil. The oil was chromatographed on silica gel using ethyl acetate as eluent, and the product fractions collected, concentrated to dryness and triturated with methylene chloride/isopropyl ether to give a white solid, 1 m.p. 185°-187° C. NMR (δ, CDCl3): 1.7 (bs, 1H), 2.8 (m, 8H), 3.6 (m, 4H), 6.9-8.0 (m, 7H).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser
  2. customprepared
  3. temperatureThe mixture was refluxed for 18 hours
  4. temperatureThe reaction was cooled
  5. custompartitioned between ethyl acetate and water
  6. customThe ethyl acetate layer was isolated
  7. washwashed with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customevaporated to an oil
  10. customThe oil was chromatographed on silica gel
  11. customthe product fractions collected
  12. concentrationconcentrated to dryness
  13. customtriturated with methylene chloride/isopropyl ether
  14. customto give a white solid, 1 m
  15. custom185°-187° C

Sources & evidence

ORD record
ord-f64b8ca3bbd34cb6be6fc3ca90e665ac
Source dataset
uspto-grants-2002_05
Patent number
US06387904B2

Reaction notes

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