N-bromobutanimide → HCID 178472368, compound

HRID 928102Notes

Reaction equation

HRID 928102 reaction equation
[OH:1][CH:2]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)[CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.C1C(=O)N([Br:26])C(=O)C1>CN(C=O)C>[Br:26][C:16]1[S:15][C:14]([CH:2]([OH:1])[C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)=[N:18][CH:17]=1.[Br:26][C:16]1[S:15][C:14]([CH:2]([OH:1])[C@@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)=[N:18][CH:17]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 70983583Ethyl 4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate

Product 2

HCID 178472368HCID 178472368, compoundHCID 178472370HCID 178472370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

The crude mixture of ethyl 4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate (34 g) was diluted with DMF (220 mL) and NBS (23 g, 129 mmol) was added. The resulting mixture was heated to 55° C. and stirred until the starting materials were consumed, at which point the heating mantle was removed. Water (220 mL) containing sodium sulfite (10 g) was added followed by EtOAc. The layers were separated, the organics washed a second time with water, then dried with MgSO4, filtered and concentrated in vacuo. The crude residue was absorbed on silica and purified by flash chromatography to afford racemic ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl)(hydroxy)methyl]cyclohexanecarboxylate as a white solid and racemic ethyl cis-4-[(5-bromo-1,3-thiazol-2-yl)(hydroxy)methyl]cyclohexanecarboxylate as a yellow oil. Characterization data for the trans isomer: MS ESI calc'd. for C13H19BrNO3S [M+H]+ 348, 350. found 348, 350. 1H NMR (600 MHz, CDCl3) δ 7.53 (d, J=4.3, 1H), 4.66 (d, J=5.0, 1H), 4.06 (q, J=7.1, 2H), 2.20-2.16 (m, 1H), 1.97 (d, J=13.3, 2H), 1.80-1.72 (m, 2H), 1.68 (d, J=12.6, 1H), 1.43-1.31 (m, 2H), 1.25-1.13 (m, 5H).

Workup

  1. additionwas added
  2. customwere consumed, at which point the heating mantle
  3. customwas removed
  4. additionWater (220 mL) containing sodium sulfite (10 g)
  5. additionwas added
  6. customThe layers were separated
  7. washthe organics washed a second time with water
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was absorbed on silica
  12. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c2f1d890926648e0aefecf3f4c9b8184
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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