N-bromobutanimide → HCID 178472352, compound

HRID 1893356Notes

Reaction equation

HRID 1893356 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Br:18]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]2[S:13][C:14]([Br:18])=[C:15]([CH3:17])[N:16]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178472356HCID 178472356, compound

Product 1

HCID 178472352HCID 178472352, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of cis/trans-4-(4-methyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester (1:5) (319 mg, 1.26 mmol) and N-bromosuccinimide (247 mg, 1.38 mmol) in N,N-dimethylformamide (1.6 ml) was stirred for 1 h at room temperature. The reaction mixture was partitioned between tert-butyl methyl ether (25 ml) and 0.1 M aqueous sodium hydroxide solution (25 ml). The layers were separated. The aqueous layer was extracted with two 25-ml portions of tert-butyl methyl ether. The combined organic layers were washed with two 25-ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound (371 mg, 89%) as light yellow solid, which was used in the next step without further purification. MS m/e: 334 ([M+H]+)

Workup

  1. customThe reaction mixture was partitioned between tert-butyl methyl ether (25 ml) and 0.1 M aqueous sodium hydroxide solution (25 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two 25-ml portions of tert-butyl methyl ether
  4. washThe combined organic layers were washed with two 25-ml portions of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d71fd789fe0463296ea83f83c3f71d1
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

Loading…