N-bromobutanimide → HCID 67467631, compound

HRID 1406293Notes

Reaction equation

HRID 1406293 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]([OH:10])([CH3:9])[CH3:8])[S:5][CH:6]=1.C1C(=O)N([Br:18])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:18][C:6]1[S:5][C:4]([C:7]([OH:10])([CH3:9])[CH3:8])=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66602564HCID 66602564, compound

Product 1

HCID 67467631HCID 67467631, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Methylthiazol-2-yl)propan-2-ol (321 mg 2.04 mmol) and NBS (404 mg 2.25 mmol) was stirred in DMF (10 mL) at room temperature for 2 hours under nitrogen. The mixture was diluted with EtOAc (50 mL) and washed with water (2×20 ml), then brine, dried over sodium sulfate and concentrated to give an oil which was purified by ISCO CombiFlash® chromatography eluting with Heptane:EtOAc (100:0 to 0:100 over 20 CV) to the product as a pale yellow oil (296 mg 61%).

Workup

  1. washwashed with water (2×20 ml)
  2. dry with materialbrine, dried over sodium sulfate
  3. concentrationconcentrated
  4. customto give an oil which
  5. customwas purified by ISCO CombiFlash® chromatography
  6. washeluting with Heptane:EtOAc (100:0 to 0:100 over 20 CV) to the product as a pale yellow oil (296 mg 61%)

Sources & evidence

ORD record
ord-ae7ee3a943b24da59b17fe2aa5ded99c
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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