Hydrochloric Acid → 4-Methyl-2-[4-(2H-tetrazol-5-yl)benzoylamino]thiazole-5-carboxylic Acid Benzylamide

HRID 45374Notes

Reaction equation

HRID 45374 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)=[N:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]2[CH:19]=[CH:20][C:21]([C:24]3[N:28]=[N:29][NH:30][N:25]=3)=[CH:22][CH:23]=2)=[N:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 593696972-(4-Cyanobenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide

Product 1

HCID 593696754-Methyl-2-[4-(2H-tetrazol-5-yl)benzoylamino]thiazole-5-carboxylic Acid BenzylamideYield 23%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(4-cyanobenzoylamino)-4-methylthiazole-5-carboxylic acid benzylamide (0.080 g, 0.21 mmol), sodium azide (0.028 g, 0.43 mmol) and ammonium chloride (0.006 g, 0.11 mmol) in N,N-dimethylformamide (5 mL) was stirred at 80° C. for 18 hours. The reaction mixture was cooled to ambient temperature, and 1 N hydrochloric acid (0.5 mL) solution was added. Ethyl acetate (10 mL) and brine (10 mL) were added to the reaction mixture. The organic layer was separated and dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrate in vacuo and the residue was purified by column chromatography to afford the title compound as a white solid in 23% yield (0.020 g); m.p.>300° C.; 1H NMR (CD3OD, 300 MHz) δ 8.20-8.09 (m, 4H), 8.45-7.20 (m, 5H), 4.51 (s, 2H), 2.55 (s, 3H); 13C NMR (CD3OD, 75 MHz) δ 163.6, 138.8, 128.4, 128.1, 127.1, 126.8, 126.5, 43.1, 15.8; MS (ES+) m/z 420.5 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrate in vacuo
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b9b7d9fc42ce4e258a4d6c7ef784513e
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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