Thionyl Chloride → Benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone

HRID 1398029Notes

Reaction equation

HRID 1398029 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:7][CH:6]([C:8]([OH:10])=O)[CH2:5][C:4]([CH3:12])([CH3:11])[O:3]1.[NH:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1.S(Cl)(Cl)=O>C(Cl)Cl>[N:14]1([C:8]([CH:6]2[CH2:5][C:4]([CH3:12])([CH3:11])[O:3][C:2]([CH3:1])([CH3:13])[CH2:7]2)=[O:10])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 867219982,2,6,6-tetramethyltetrahydro-2H-pyran-4-carboxylic acidHCID 178418385HCID 178418385, compound

Product 1

HCID 86721999Benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,2,6,6-tetramethyl-tetrahydro-pyran-4-carboxylic acid (1.4 g, 6.8 mmol) and benzotriazole (2.4 g, 20.3 mmol) in 34 mL of DCM was added thionyl chloride (0.55 mL, 7.4 mmol) dropwise and the mixture was allowed to stir for 8 hrs at RT. The mixture was filtered to remove the ppt and the filtrate washed with saturated NaHCO3 (2×40 mL) and then brine (50 mL). The organic layer was dried over Na2SO4 and concentrated to give 1.9 g (97%) of a white ppt.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the ppt
  3. washthe filtrate washed with saturated NaHCO3 (2×40 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give 1.9 g (97%) of a white ppt

Sources & evidence

ORD record
ord-260622d1f06d4d92a88cc7a455987cd1
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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