Sodium Chlorite → 2-Benzoylamino-4-chlorothiazole-5-carboxylic Acid

HRID 45319Notes

Reaction equation

HRID 45319 reaction equation
Cl([O-])=[O:2].[Na+].[Cl:5][C:6]1[N:7]=[C:8]([NH:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:9][C:10]=1[CH:11]=[O:12]>O.C(#N)C.CC(O)(C)C.CC(=CC)C>[C:14]([NH:13][C:8]1[S:9][C:10]([C:11]([OH:2])=[O:12])=[C:6]([Cl:5])[N:7]=1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 2

HCID 23668197Sodium ChloriteHCID 86642515N-(4-chloro-5-formylthiazol-2-yl)benzamide

Product 1

HCID 866425162-Benzoylamino-4-chlorothiazole-5-carboxylic AcidYield 17%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

A solution of sodium chlorite (2.20 g, 19.40 mmol) and NaH2PO4 (2.32 g, 19.10 mmol) in water (10 mL) was added to a mixture of N-(4-chloro-5-formylthiazol-2-yl)benzamide (0.52 g, 1.95 mmol) in acetonitrile (20 mL), t-BuOH (20 mL) and 2-methyl-2-butene (4 mL) at 0° C. The mixture was stirred for 1 h, then extracted with chloroform, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give the crude product in 17% yield (0.097 g), which was used for next step without purification; MS (ES+) m/z 283.3 (M+1).

Workup

  1. extractionextracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7a910167793042148c7196fb19b9be4c
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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