Hydrochloric Acid → HCID 70102975, compound

HRID 1602493Notes

Reaction equation

HRID 1602493 reaction equation
Br.[C:2]([C:6]1[N:7]=[C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([O:19]C)=[O:18])[S:9][CH:10]=1)([CH3:5])([CH3:4])[CH3:3].[ClH:24]>CO>[ClH:24].[C:2]([C:6]1[N:7]=[C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([OH:19])=[O:18])[S:9][CH:10]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 19611488HCID 19611488, compound

Product 1

HCID 70102975HCID 70102975, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-[2-(4-tert-butyl-2-thiazolyl)ethoxy]benzoate hydrobromide (102 mg, 0.25 mmol), methanol (1 ml) and 6 N hydrochloric acid (0.5 ml) was stirred at 60° C. for 2 hours, 6 N hydrochloric acid (1 ml) was added, and the mixture was and stirred at 110° C. for 2 hours. The reaction solution was cooled and concentrated under reduced pressure. The resulting solid material was collected by filtration and washed with acetonitrile and diethyl ether in that order to give 3-[2-(4-tert-butyl-2-thiazolyl)ethoxy]benzoic acid hydrochloride (69 mg, 0.20 mmol, 80%).

Workup

  1. stirringstirred at 110° C. for 2 hours
  2. temperatureThe reaction solution was cooled
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe resulting solid material was collected by filtration
  5. washwashed with acetonitrile and diethyl ether in that order

Sources & evidence

ORD record
ord-78d3393dbe674e5a8cad0c3524c90944
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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