Thionyl Chloride → HCID 178458524, compound

HRID 1644602Notes

Reaction equation

HRID 1644602 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:29])[CH3:28])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][C:20]([CH2:23]O)=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:32])=O>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:29])[CH3:28])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][C:20]([CH2:23][Cl:32])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178458528HCID 178458528, compound

Product 1

HCID 178458524HCID 178458524, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of {2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridin-5-yl}methanol (0.11 g) and thionyl chloride (0.1 g) in chloroform (10 ml) was heated under reflux for 3 hr. The reaction mixture was concentrated, and saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated to give the title compound (0.11 g, yield 96%) as colorless crystals. purity 85%. M+H: 408. 1H NMR (CDCl3) δ: 1.51 (6H, d, J=6.0 Hz), 3.97-4.15 (2H, m), 4.72-4.81 (1H, m), 5.16 (2H, s), 7.00-7.06 (1H, m), 7.07-7.12 (1H, m), 7.31-7.51 (6H, m), 8.07 (1H, d, J=7.9 Hz), 8.20 (1H, s).

Workup

  1. temperatureunder reflux for 3 hr
  2. concentrationThe reaction mixture was concentrated
  3. additionsaturated aqueous sodium hydrogencarbonate solution was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b227f8ec508149558ed241bddd4a71f0
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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