Tetrahydrofuran → HCID 22144527, compound

HRID 1824798Notes

Reaction equation

HRID 1824798 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[C:3]=1C(O)=O.[OH-:24].[Na+].C1C[O:29]CC1>O>[C:1]([C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1)([OH:29])=[O:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22144538HCID 22144538, compound

Product 1

HCID 22144527HCID 22144527, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-methylcarboxy-6-methoxy-2-(4-methoxy-phenyl)-benzothiazole (0.37 g, 1.12 mmol) in THF (6 mL) and water (3 mL) was added 1N sodium hydroxide (2.24 mL, 2.24 mmol) and the solution was stirred at room temperature for 24 h. THF was then evaporated. 1 N HCl was added to PH 1. The solid was collected by filtration and washed with water to give 4-carboxy-6-methoxy-2-(4-methoxy-phenyl)benzothiazole (0.29 g, 82% yield) as a white solid. Mass spec: MH+=316.

Workup

  1. customTHF was then evaporated
  2. addition1 N HCl was added to PH 1
  3. filtrationThe solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-0c8b218f582a4a1b87aaebbc2af92ffb
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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