Thionyl Chloride → HCID 59864270, compound

HRID 1674497Notes

Reaction equation

HRID 1674497 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:22]=[CH:21][C:10]3[CH2:11][CH2:12][N:13]([CH:16]([CH3:20])[CH2:17][CH2:18]O)[CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:23])=[N:3]1.S(Cl)([Cl:26])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:26][CH2:18][CH2:17][CH:16]([N:13]1[CH2:12][CH2:11][C:10]2[CH:21]=[CH:22][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:23])[CH:5]=3)=[CH:8][C:9]=2[CH2:15][CH2:14]1)[CH3:20]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 598642713-[7-(1,3-Dimethyl-1H-pyrazol-5-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-1-butanol2×

Product 1

HCID 59864270HCID 59864270, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 3-[7-(1,3-dimethyl-1H-pyrazol-5-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-1-butanol (0.25 g) (intermediate 9) in chloroform (8 ml), at room temperature, thionyl chloride (0.11 ml) was added dropwise. After 2h, saturated aqueous sodium hydrogencarbonate (5 ml) was added, the reaction mixture was extracted with dichloromethane (15 ml), the organic phase dried with sodium sulphate and the solvent evaporated under reduced pressure. The crude product was purified by chromatography on silica gel with 80% cyclohexane-ethyl acetate to give the title compound (0.23 g) as a white solid.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane (15 ml)
  2. dry with materialthe organic phase dried with sodium sulphate
  3. customthe solvent evaporated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel with 80% cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-c8160d7e6c47422ab531dbab983a6874
Source dataset
uspto-grants-2011_08
Patent number
US08003638B2

Reaction notes

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