Pyridine → N-(4-methylcyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide

HRID 35255

Reaction equation

HRID 35255 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][CH2:9][C:10](O)=[S:11])=[N:5][N:4]=[N:3]1.N1C=CC=CC=1.BrC(OC)=O.[CH3:24][CH:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1>O1CCCC1>[CH3:24][CH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:10](=[S:11])[CH2:9][CH2:8][CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 806044-MethylcyclohexylamineHCID 15389422Methyl bromoformateHCID 178482013HCID 178482013, compound

Product 1

HCID 53879184N-(4-methylcyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramideYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tetrahydrofuran (50 ml) are added 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) and pyridine (50 mmole), and thereto is added dropwide with stirring methyl bromoformate (50 mmole) with keeping the inner temperature at 5°-15° C. by ice-cooling, and thereafter, the mixture is stirred at room temperature for one hour. To the mixture is added 4-methylcyclohexylamine (55 mmole), and the mixture is further stirred for 3 hours. After the reaction, the solvent is distilled off under reduced pressure, and the residue is dissolved in chloroform. The chloroform layer is washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order, and dried over sodium sulfate. Inorganic materials are filtered off and the mother liquor is concentrated. The resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-(4-methylcyclohexyl)-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 45%).

Workup

  1. customat 5°-15° C.
  2. temperaturecooling
  3. stirringthe mixture is further stirred for 3 hours
  4. customAfter the reaction
  5. distillationthe solvent is distilled off under reduced pressure
  6. dissolutionthe residue is dissolved in chloroform
  7. washThe chloroform layer is washed with dilute aqueous sodium hydroxide solution, diluted hydrochloric acid and water in order
  8. dry with materialdried over sodium sulfate
  9. filtrationInorganic materials are filtered off
  10. concentrationthe mother liquor is concentrated
  11. washThe resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

Sources & evidence

ORD record
ord-825401dce0eb47f9a136bed2c5c2f8ea
Source dataset
uspto-grants-1988_08
Patent number
US04766120

Linked notes

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