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

HRID 1039937Notes

Reaction equation

HRID 1039937 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.[Br:17]N1C(=O)CCC1=O>CN(C=O)C>[Br:17][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

4

Reactant 2

HCID 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 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The product of Step 1 (60.5 g, 251 mmol) was diluted with DMF (365 mL). N-bromosuccinimide (49.1 g, 276 mmol) was added, and the solution was heated to 50° C. and stirred for 2 h. The reaction was removed from heat and cooled to 45° C. and H2O (600 mL) containing 15.8 g Na2SO3 was added dropwise affording a solid. The mixture was stirred at room temperature for 1 h, then filtered and washed 2× with H2O (300 mL). The cake was dried overnight under a nitrogen bag to afford 8-(5-bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (68.2 g, 85%) as a white solid.

Workup

  1. customThe reaction was removed
  2. temperaturefrom heat
  3. temperaturecooled to 45° C.
  4. additionH2O (600 mL) containing 15.8 g Na2SO3
  5. additionwas added dropwise
  6. customaffording a solid
  7. stirringThe mixture was stirred at room temperature for 1 h
  8. filtrationfiltered
  9. washwashed 2× with H2O (300 mL)
  10. customThe cake was dried overnight under a nitrogen bag

Sources & evidence

ORD record
ord-f357ab0e57a74e1a9956aa75f15c51c7
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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