Sodium Hydroxide → Methyl-6-methoxy-2-phenyl-5-benzothiazolcarboxylate

HRID 1459597Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A 2 liter round bottom flask was charged with 81 grams (246 mmol) potassium ferricyanide in 300 mL of water, the solution was warmed to 55° C. A solution of 14.78 grams (49 mmol) methyl-2-methoxy-5-benzthioamido-benzoate in 200 mL of methanol and 100 mL aqueous sodium hydroxide solution [13.7 gm (343 mmol) NaOH/100 mL] was then added. A yellow precipitate was soon deposited. The mixture was stirred at 60° C. for 1.5 hours. The reaction mixture was partitioned between 1 liter ethyl acetate and 300 mL 3.4N HCl (aqueous). The organic phase was washed with water and brine solution and then dried over sodium sulfate. After filtration, the filtrate was evaporated and the residue, as a mixture of carboxylates, was used directly in the next step. (affords 12.9 grams crude)

Workup

customThe reaction mixture was partitioned between 1 liter ethyl acetate and 300 mL 3.4N HCl (aqueous)
washThe organic phase was washed with water and brine solution
dry with materialdried over sodium sulfate
filtrationAfter filtration
customthe filtrate was evaporated
additionthe residue, as a mixture of carboxylates
custom(affords 12.9 grams crude)

Sources & evidence

ORD record: ord-96a8ec548ca2422b9d9b1f2b0da0acaa
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854262

Reaction notes

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