N-bromobutanimide → HCID 59558255, compound

HRID 1755503Notes

Reaction equation

HRID 1755503 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:20]N1C(=O)CCC1=O>CN(C=O)C>[Br:20][C:16]1[S:17][CH:18]=[CH:19][C:15]=1[C:12]1[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 21881190HCID 21881190, compound

Product 1

HCID 59558255HCID 59558255, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a three necked flask under argon, 1.40 g (5.14 mmol) of YKP67 in 40 mL of DMF are cooled to 0° C. 915 mg (5.14 mmol, 1 eq.) of N-bromosuccinimide are solubilised in 20 mL of mixture [DMF/MeOH:1/1]. This solution of NBS (protected from light) is then added drop by drop (30 min) into the reaction medium. The temperature of the medium is then left to rise to ambient temperature over 2 h. The medium is hydrolysed with a 1 mol·L−1 HCL solution and extracted with ethyl ether. The combined organic phases are washed with a saturated NaCl solution then dried on anhydrous Na2SO4. After drying on Na2SO4, filtration and evaporation of the solvent, the purification is carried out on silica column with cyclohexane. 1.58 g of final compound YKP69 in the form of a translucent oil (yield of 85.7%) are obtained.

Workup

  1. waitThe temperature of the medium is then left
  2. extractionextracted with ethyl ether
  3. washThe combined organic phases are washed with a saturated NaCl solution
  4. dry with materialthen dried on anhydrous Na2SO4
  5. customAfter drying on Na2SO4, filtration and evaporation of the solvent
  6. customthe purification

Sources & evidence

ORD record
ord-7b39029118354df9aeccac6befa35f1d
Source dataset
uspto-grants-2015_10
Patent number
US09171676B2

Reaction notes

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