Acetonitrile → HCID 57447078, compound

HRID 521326Notes

Reaction equation

HRID 521326 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]([CH3:20])=[C:4]([CH3:21])[N:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].C(#N)C>O>[CH3:21][C:4]1[N:3]2[N:22]=[N:23][N:24]=[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]=1[CH3:20]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 33557Sodium AzideHCID 21585214Cerium trichloride heptahydrateHCID 57455392Ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butyrate

Product 1

HCID 57447078HCID 57447078, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butyrate (86.2 g, 0.276 mol), sodium azide (35.49 g, 0.552 mol), and cerium chloride heptahydrate (50.86 g, 0.138 mol) were triturated in a 9:1 mixture of acetonitrile:water (1012 mL). The reaction mixture was stirred and heated to reflux for 18 hours. The reaction was filtered and the yellow filtrate was concentrated under reduced pressure to yield 90.94 g of crude product. The material was triturated at 95° C. with 360 mL ethyl acetate and filtered. The filtrate produced pale yellow crystals at ambient temperature to afford 64.3 g of ethyl 4-[(5,6-dimethyl-8-nitrotetrazolo[1,5-a]pyridin-7-yl)amino]butyrate as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. filtrationThe reaction was filtered
  4. concentrationthe yellow filtrate was concentrated under reduced pressure
  5. customto yield 90.94 g of crude product
  6. customThe material was triturated at 95° C. with 360 mL ethyl acetate
  7. filtrationfiltered
  8. customThe filtrate produced pale yellow crystals at ambient temperature

Sources & evidence

ORD record
ord-a69fc5e1657b48da89de1763916b591b
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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