Thionyl Chloride → HCID 68427838, compound

HRID 642387Notes

Reaction equation

HRID 642387 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:11](CC2C=CC(OC)=CC=2OC)[CH2:10][C:9]2[N:23]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=3)[S:25][C:8]=2[C:7]1=[O:36])=[O:5])[CH3:2].S(Cl)(Cl)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:23]=[C:24]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:30][CH:31]=3)[S:25][C:8]=2[C:7]=1[OH:36])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68428251HCID 68428251, compound

Product 1

HCID 68427838HCID 68427838, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-tert-Butyl-phenyl)-5-(2,4-dimethoxy-benzyl)-7-oxo-4,5,6,7-tetrahydro-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (0.5 g, 0.98 mmol) was dissolved in 6.7 mL of anhydrous dichloromethane. To the solution was added 108 μL of thionyl chloride, and the reaction was stirred for 5 h. The solution was filtered on a fine glass frit filter to collect a white solid precipitate. The solid was washed twice with cold dichloromethane and then partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to produce 0.21 g of a yellow solid. MS: (+) m/z 357.0 (M+1).

Workup

  1. filtrationThe solution was filtered on a fine glass frit
  2. filtrationfilter
  3. customto collect a white solid precipitate
  4. washThe solid was washed twice with cold dichloromethane
  5. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  6. washThe organic fraction was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c41269fde4a3401a8dafaa215a9ad1bd
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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