HCID 21893516, compound → HCID 21893483, compound

HRID 1167213Notes

Reaction equation

HRID 1167213 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[NH:10][C:9]2=O)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[NH:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21893516HCID 21893516, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21893483HCID 21893483, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

4-(4-Bromophenyl)-1,1,3-trioxotetrahydro-1,2-thiazine: To a 0° C. solution of 9.0 mL (9.0 mmol) of a 1.0 M tetrahydrofuran solution of potassium tert-butoxide in 15 mL of tetrahydrofuran was added a solution of 1.7 g (4.5 mmol) of material from Step D in 14 mL of tetrahydrofuran dropwise over 30 minutes. After stirring at 0° C. for two hours, the cooling bath was removed and stirring continued for 30 minutes. The mixture was diluted with 25 mL of water and extracted two times with 10 mL each of ethyl ether. The aqueous portion was acidified to pH 2 with 10% aqueous sodium bisulfate and extracted four times with 20 mL each of ethyl acetate. The combined ethyl acetate layers were dried (MgSO4), filtered and concentrated in vacuo. Chromatography (75 g silica gel, 0.25% acetic acid/40% acetone/hexanes) of the residue affords 0.2 g (17%) of the title compound.

Workup

  1. customthe cooling bath was removed
  2. stirringstirring
  3. waitcontinued for 30 minutes
  4. additionThe mixture was diluted with 25 mL of water
  5. extractionextracted two times with 10 mL each of ethyl ether
  6. extractionextracted four times with 20 mL each of ethyl acetate
  7. dry with materialThe combined ethyl acetate layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1d4c204d0724a4f8831a7eeff620e60
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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