Phosphorus oxychloride → 2-Benzyl-4-(2-chloro-4-pyridyl)thiazole

HRID 2309804Notes

Reaction equation

HRID 2309804 reaction equation
[C:1]1([CH2:7][C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][N+:16]([O-])=[CH:15][CH:14]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:22])=O>>[CH2:7]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:22])[CH:14]=2)[N:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 142310544-[2-(Phenylmethyl)-4-thiazolyl]pyridine-1-oxide

Product 1

HCID 142310552-Benzyl-4-(2-chloro-4-pyridyl)thiazoleYield 31%

Procedure

A suspension of 4-[2-(phenylmethyl)-4-thiazolyl]pyridine-1-oxide (1.00 g, 0.0037 mol) in phosphorous oxychloride (10.0 g) was warmed on a steam bath overnight. After cooling the reaction mixture was concentrated and the residue treated with an excess of aqueous sodium bicarbonate. The tan precipitate was collected, taken up in methylene chloride (15 mL) and ether (75 mL), and filtered through celite. The filtrate was concentrated to a total volume of 10 mL and diluted with hexane (50 mL). The product which crystallized on standing was collected and dried to afford 2-benzyl-4-(2-chloro-4-pyridyl)thiazole (325 mg, 31%). mp. 104°-106° C.

Workup

  1. temperaturewas warmed on a steam bath overnight
  2. temperatureAfter cooling the reaction mixture
  3. concentrationwas concentrated
  4. additionthe residue treated with an excess of aqueous sodium bicarbonate
  5. customThe tan precipitate was collected
  6. filtrationether (75 mL), and filtered through celite
  7. concentrationThe filtrate was concentrated to a total volume of 10 mL
  8. additiondiluted with hexane (50 mL)
  9. customThe product which crystallized on standing
  10. customwas collected
  11. customdried

Sources & evidence

ORD record
ord-21df7b50414541a9b87d902ea99e67f4
Source dataset
uspto-grants-1987_09
Patent number
US04697012

Reaction notes

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