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

HRID 840606Notes

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 3.4 N 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 3.4 N 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-2951c691a6434918b143bcb0c7992c57
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369074B1

Reaction notes

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