Sodium Sulfite → 8-(5-Bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1039965Notes

Reaction equation

HRID 1039965 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([OH:16])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1.C1C(=O)N([Br:24])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[Br:24][C:5]1[S:1][C:2]([C:6]2([OH:16])[CH2:7][CH2:8][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:14][CH2:15]2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 578033298-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 672560328-(5-Bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-olYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (15.0 g, 62.2 mmol) in DMF (75 mL) was added NBS (6.9 g, 55 mmol) and the solution warmed to 45° C. for 8 hours. The solution was treated with Na2SO3 (3.9 g, 31 mmol) in H2O (150 mL) and the resulting slurry was filtered and washed with water (70 mL) to afford 8-(5-bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol as a white solid (16.8 g, 52.5 mmol).

Workup

  1. filtrationthe resulting slurry was filtered
  2. washwashed with water (70 mL)

Sources & evidence

ORD record
ord-f5fb9523fe0d45e09630146c9907d810
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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