N-bromobutanimide → HCID 89689977, compound

HRID 714033Notes

Reaction equation

HRID 714033 reaction equation
[N:1]12[CH2:11]CCN=C1CCCCC2.BrN1[C:17](=[O:18])CCC1=O.[CH2:20]([O:27][C:28]1[C:29]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=2)=[CH:30][C:31]([CH2:51][CH3:52])=[C:32]([CH:50]=1)[O:33][CH2:34][CH2:35][CH2:36][O:37][C:38]1[C:39]([CH2:47][CH2:48][CH3:49])=[C:40]([CH:44]=[CH:45][CH:46]=1)C(N)=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(=O)(=O)(O)[O-:61].[Na+]>CO.O>[CH2:20]([O:27][C:28]1[C:29]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=2)=[CH:30][C:31]([CH2:51][CH3:52])=[C:32]([CH:50]=1)[O:33][CH2:34][CH2:35][CH2:36][O:37][C:38]1[C:39]([CH2:47][CH2:48][CH3:49])=[C:40]([NH:1][C:11](=[O:61])[O:18][CH3:17])[CH:44]=[CH:45][CH:46]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 67184N-bromobutanimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516919Sodium BisulfateHCID 89690029HCID 89690029, compound

Product 1

HCID 89689977HCID 89689977, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sequentially add 1,8-diazabicyclo[5.4.0]undec-7-ene (51.6 mL, 345 mmol) and N-bromosuccinimide (34.6 g, 194 mmol) to a mechanically stirred suspension of 3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-benzamide (62.0 g, 114 mmol) in MeOH (620 mL) during which time the temperature raises from −4.1° C. to −3.2° C. over 1 min. Stir the reaction at −5° C. to −10° C. for 22 h. Add a solution of sodium bisulfate (25.1 g, 209 mmol, in 25 mL water) dropwise with stirring. Add water (620 mL) dropwise and stir 30 min at 10° C. Filter the suspension on a glass frit, wash the collected solid with water, and dry under vacuum to yield the title compound (65.8 g, quantitative) as an off-white powder. ES/MS m/z 572 (M+1).

Workup

  1. temperatureraises from −4.1° C. to −3.2° C. over 1 min
  2. customthe reaction at −5° C. to −10° C. for 22 h
  3. stirringwith stirring
  4. filtrationFilter the suspension on a glass frit
  5. washwash the collected solid with water
  6. customdry under vacuum

Sources & evidence

ORD record
ord-d49f9ab4447c409b8c0a1ec0f4674977
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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