Thionyl Chloride → HCID 69059374, compound

HRID 734833Notes

Reaction equation

HRID 734833 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]3[CH:30]=[CH:29][C:23]4[S:24][C:25]([CH2:27]O)=[CH:26][C:22]=4[CH:21]=3)=[N:16][CH:17]=2)=[CH:8][CH:7]=1>C(Cl)Cl>[Cl:3][CH2:27][C:25]1[S:24][C:23]2[CH:29]=[CH:30][C:20]([C:19]#[C:18][C:15]3[CH:14]=[CH:13][C:12]([C:9]4[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=4)=[CH:17][N:16]=3)=[CH:21][C:22]=2[CH:26]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69059825HCID 69059825, compound

Product 1

HCID 69059374HCID 69059374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.07 mL (15 mmol) of thionyl chloride was added to a solution of 1.1 g (2.93 mmol) of {5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]benzo[b]thiophen-2-yl}methanol in 20 mL of DCM cooled to 0° C. and the reaction mixture was stirred for 70 hours at RT. It was evaporated down in vacuo, the residue was combined with semisaturated sodium bicarbonate solution, extracted exhaustively with DCM, and the combined organic phases were washed twice with water and dried over magnesium sulfate. After the desiccant and solvent had been eliminated, the residue was purified by chromatography (silica gel, PE/EtOAc 7:3). Yield: 0.65 g (56% of theoretical); C22H13Cl2NS (M=394.317); calc.: molpeak (M+H)+: 394/396/398 (2Cl); found: molpeak (M+H)+: 394/396/398 (2Cl); HPLC-MS: 7.6 minutes (method B).

Workup

  1. customIt was evaporated down in vacuo
  2. extractionextracted exhaustively with DCM
  3. washthe combined organic phases were washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. customthe residue was purified by chromatography (silica gel, PE/EtOAc 7:3)
  6. custom7.6 minutes (method B)

Sources & evidence

ORD record
ord-c8de6c7320004c2b8d48a7511f64ef1f
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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