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

HRID 1358232Notes

Reaction equation

HRID 1358232 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].Cl>[OH-].[Na+].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 2

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

Product 1

HCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 178511488HCID 178511488, compoundCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
10 °C

Procedure

A solution of (2-methoxy-5-morpholin-4-yl-phenylamino)-thioxo-acetic acid (4) in 1N NaOH is added to a solution of potassium ferricyanide in water at a rate that the temperature does not exceed 10° C. The mixture is stirred for 3 hours at 10° C. and concentrated hydrochloric acid is added until pH 1 was reached. Filtration of the precipitate and drying yielded 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (5). A suspension of the compound of formula (5) and 1.1′-carbonyl-diimidazole in dimethylformamide is stirred at room temperature for about one hour. A compound of formula (6), for example benzylamine, is added, stirring is continued and after about 20 hours water is added. After extraction with ethyl acetate and chromatography on silicagel with dichloromethane/ethyl acetate is yielded a compound of formula I.

Workup

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

Sources & evidence

ORD record
ord-a71774fabe6b4ad7b077df685c7bd90e
Source dataset
uspto-grants-2003_07
Patent number
US06596718B1

Reaction notes

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