N-bromobutanimide → HCID 11539960, compound

HRID 229378Notes

Reaction equation

HRID 229378 reaction equation
[CH2:1]([CH:3]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=2)(=[O:15])=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:24])[CH:10]=2)[N:5]2[CH:25]=[CH:26][CH:27]=[C:4]12)[CH3:2].[Br:28]N1C(=O)CCC1=O>C(Cl)Cl>[Br:28][C:25]1[N:5]2[C:6]3[C:11]([N:12]([S:13]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=4)(=[O:15])=[O:14])[CH:3]([CH2:1][CH3:2])[C:4]2=[CH:27][CH:26]=1)=[CH:10][C:9]([F:24])=[CH:8][CH:7]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11552776HCID 11552776, compound

Product 1

HCID 11539960HCID 11539960, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a 50 ml round bottom flask with addition funnel was added 30 ml of methylene chloride and 0.38 g (1 mmol) of the product from Example 19. The flask was cooled to −78° C. and a solution of 0.18 g (1 mmol) of N-bromosuccinimide in 10 ml of methylene chloride was slowly added via addition funnel. After addition was complete, the reaction was allowed to stir at this temperature for 1 hr, then cooling removed. When the reaction had warmed to room temperature it was extracted with 20 ml of saturated sodium bicarbonate solution and separated. The aqueous layer was extracted twice with 10 ml of methylene chloride and the combined organic layers were dried (MgSO4) and concentrated. The crude solid was subjected to column chromatography eluting with 40% ethyl acetate:hexane to yield 0.32 g (69%) of solid which was crystallized from ethyl acetate:hexane to produce colorless crystals, mp 119° C. (dec).

Workup

  1. additionTo a 50 ml round bottom flask with addition funnel
  2. additionAfter addition
  3. temperaturecooling
  4. customremoved
  5. temperatureWhen the reaction had warmed to room temperature it
  6. extractionwas extracted with 20 ml of saturated sodium bicarbonate solution
  7. customseparated
  8. extractionThe aqueous layer was extracted twice with 10 ml of methylene chloride
  9. dry with materialthe combined organic layers were dried (MgSO4)
  10. concentrationconcentrated
  11. washeluting with 40% ethyl acetate

Sources & evidence

ORD record
ord-0d6695a1321948e1b33fd4a27dc1cb5c
Source dataset
uspto-grants-2009_07
Patent number
US07563793B2

Reaction notes

Loading…