Hydrochloric Acid → {2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetic acid

HRID 1710794Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([CH2:18][C:19]([O:21]CC)=[O:20])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([CH2:18][C:19]([OH:21])=[O:20])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetate i102 (0.5 g, 1.41 mmol, 1 eq) and sodium hydroxide (0.2 g, 5 mmol, 3.5 eq) in ethanol (15 ml) is stirred at 60° C. for 1 h 30. A 1 N hydrochloric acid solution (6 ml) is added and ethanol is removed under vacuum. The residue is dissolved in ethyl acetate (200 ml). The organic layer is washed with water (2×50 ml), brine, dried over magnesium sulfate, filtered and concentrated to yield 0.5 g of {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetic acid i103 as a white solid. This solid is used as such in the next step.

Workup

customethanol is removed under vacuum
dissolutionThe residue is dissolved in ethyl acetate (200 ml)
washThe organic layer is washed with water (2×50 ml), brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f9369559a05944eb83feb0efaa7d2d70
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790720B2

Reaction notes

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