Thionyl Chloride → HCID 136343974, compound

HRID 1847216Notes

Reaction equation

HRID 1847216 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:11](CC2C=CC(OC)=CC=2OC)[CH2:10][C:9]2[S:23][N:24]=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:8]=2[C:7]1=[O:32])=[O:5])[CH3:2].O=S(Cl)Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:32])=[C:8]2[C:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[N:24][S:23][C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68629396HCID 68629396, compound

Product 1

HCID 136343974HCID 136343974, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2,4-dimethoxy-benzyl)-4-oxo-3-phenyl-4,5,6,7-tetrahydro-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (5.42 g, 11.99 mmol) in CH2Cl2 was added SOCl2 (1.31 mL, 17.98 mmol) and the mixture was stirred at r.t. After 3 h the mixture was filtered and the filter cake was washed with hexanes/CH2Cl2(4/1, 12 mL). The solid was then suspended in sat. NaHCO3 (200 mL) and the mixture extracted with EtOAc (3×200 mL). The combined organic layers were washed with brine, water, dried over MgSO4, and concentrated in vacuo to give the title compound as yellow solid (2.56 g): MS (m/z) 301.1 (M+1).

Workup

  1. filtrationAfter 3 h the mixture was filtered
  2. washthe filter cake was washed with hexanes/CH2Cl2(4/1, 12 mL)
  3. extractionthe mixture extracted with EtOAc (3×200 mL)
  4. washThe combined organic layers were washed with brine, water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d690d205afbf4801ad3b6b6b5e6c0069
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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