Water → HCID 58124908, compound

HRID 1971729Notes

Reaction equation

HRID 1971729 reaction equation
[C:1]([N:5]1[C:29](=[O:30])[C:28]2[N:13]3[CH2:14][CH2:15][C:16]4[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:21]=4[C:12]3=[CH:11][C:10]=2[CH2:9][O:8][CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Br:31]N1C(=O)CCC1=O.O>CN(C=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[C:1]([N:5]1[C:29](=[O:30])[C:28]2[N:13]3[CH2:14][CH2:15][C:16]4[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[CH:20][C:21]=4[C:12]3=[C:11]([Br:31])[C:10]=2[CH2:9][O:8][CH2:7][CH2:6]1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58124925HCID 58124925, compound

Product 1

HCID 58124908HCID 58124908, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 24477Sodium ThiosulfateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 180 mg of 18c in 2 ml of DMF was added 85 mg of N-bromosuccinimide. The mixture was stirred for ½ hr at RT. 3 ml of water was added and two drops of sat. aq. Na2S2O3 and the mixture was stirred for ½ hr. The precipitate was filtered and washed with water, dried and then triturated with diisopropyl ether, to provide 175 mg of 18d as white crystalline material. Mp 160-162° C.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-7128a74a8a5d4e849f36b7d48b275424
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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