Diethyl Ether → [4-(Chloromethyl)-1,3-thiazol-2-yl]methanol hydrochloride

HRID 1736659Notes

Reaction equation

HRID 1736659 reaction equation
C([O:4][CH2:5][C:6]1[S:7][CH2:8][C:9]([CH2:12][Cl:13])(O)[N:10]=1)(=O)C.C(OCC)C>Cl.C(O)(C)C>[ClH:13].[Cl:13][CH2:12][C:9]1[N:10]=[C:6]([CH2:5][OH:4])[S:7][CH:8]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 117908272-Acetoxymethyl-4-chloromethyl-4-hydroxythiazoline

Product 1

HCID 21464457[4-(Chloromethyl)-1,3-thiazol-2-yl]methanol hydrochlorideYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

7.48 g of 2-acetoxymethyl-4-chloromethyl-4-hydroxythiazoline, prepared according to either Example 3 or 4, was suspended in 20 ml of 5N hydrogen chloride in isopropanol and heated to reflux for 45 minutes. The suspension was cooled in an ice bath and 30 ml of diethyl ether added dropwise over 30 minutes. The slurry was stirred a further 30 minutes at 0° C. and the precipitate filtered, washed with ether and dried under vacuum. 4-chloromethyl-2-hydroxymethylthiazole hydrochloride, 6.22 g (93% yield) was obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 45 minutes
  3. temperatureThe suspension was cooled in an ice bath
  4. filtrationthe precipitate filtered
  5. washwashed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3512514b84204a2a929dcc81f1bee325
Source dataset
uspto-grants-1996_07
Patent number
US05541335

Reaction notes

Loading…