Hydrochloric Acid → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid

HRID 1358236Notes

Reaction equation

HRID 1358236 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16](=[S:20])[C:17]([OH:19])=[O:18].[OH-].[Na+].Cl>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH3:1][O:2][C:3]1[C:4]2[N:15]=[C:16]([C:17]([OH:19])=[O:18])[S:20][C:5]=2[C:6]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21919264(2-Methoxy-5-morpholin-4-yl-phenylamino)-thioxo-acetic acid

Product 1

HCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acidYield 84.5%

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 10.5 g (35.4 mmol) (2-methoxy-5-morpholin-4-yl-phenylamino)-thioxo-acetic acid in 248 ml (248 mmol) 1N NaOH was added drop-wise to a solution of 40.1 g (119 mmol) potassium ferricyanide in 119 ml water at a rate that the temperature did not exceed 10° C. The mixture was stirred for 3 hours at 10° C. and concentrated hydrochloric acid was added until pH 1 was reached. Filtration of the precipitate and drying yielded 8.80 g (84%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid as yellow crystals with mp.: 99-100° C., MS m/e (%)): 295 (M+H+, 100).

Workup

  1. customdid not exceed 10° C
  2. filtrationFiltration of the precipitate
  3. customdrying

Sources & evidence

ORD record
ord-4a84b6728ff1484481899b0614001eb9
Source dataset
uspto-grants-2003_07
Patent number
US06596718B1

Reaction notes

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