Thionyl Chloride → 5-(3-Chloropropyl)-2-phenylthiazole-4-carbonyl chloride

HRID 453301Notes

Reaction equation

HRID 453301 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:16]([OH:18])=O.[Li+].[Cl-:20].S(Cl)([Cl:23])=O>>[Cl:20][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:16]([Cl:23])=[O:18]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 433294Lithium ChlorideHCID 585518715-(3-Hydroxypropyl)-2-phenylthiazole-4-carboxylic acid

Product 1

HCID 585519005-(3-Chloropropyl)-2-phenylthiazole-4-carbonyl chlorideYield 99%

Procedure

A mixture of 5-(3-hydroxypropyl)-2-phenylthiazole-4-carboxylic acid (850 mg, 3.2 mmol) and LiCl (3.2 mmol) in thionyl chloride (10 mL) was heated at reflux for 16 h then concentrated to dryness. The crude product was dissolved in EtOAc, washed with brine, dried (MgSO4), and concentrated under reduced pressure to give 5-(3-chloropropyl)-2-phenylthiazole-4-carbonyl chloride (906 mg, 99% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. concentrationthen concentrated to dryness
  4. dissolutionThe crude product was dissolved in EtOAc
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9517eebeae774af589db741702622aa5
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

Loading…