Thionyl Chloride → HCID 67361244, compound

HRID 404401Notes

Reaction equation

HRID 404401 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][C:11]=1[C:18]1[N:22]([CH:23]([CH3:25])[CH3:24])[CH:21]=[N:20][N:19]=1.O=S(Cl)[Cl:28]>C(Cl)Cl.CN(C=O)C>[Cl:28][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[C:11]([C:18]2[N:22]([CH:23]([CH3:25])[CH3:24])[CH:21]=[N:20][N:19]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 67361195HCID 67361195, compound

Product 1

HCID 67361244HCID 67361244, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 29.5 (60 mg, 176 μmol) in DCM was added one drop of DMF followed by SOCl2(63 mg, 527 μmol). The mixture was stirred at room temperature for 2.0 hours. After removal of organic solvents under reduced pressure, purification of the residue by flash chromatography on silica gel with 0-5% MeOH/EtOAc provided 29.6 as a colorless oil (44 mg, 70%).

Workup

  1. customAfter removal of organic solvents
  2. customunder reduced pressure, purification of the residue by flash chromatography on silica gel with 0-5% MeOH/EtOAc

Sources & evidence

ORD record
ord-ed13807bbd8d4670a24545eedee1175e
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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