Acetonitrile → HCID 57447078, compound

HRID 1623107Notes

Reaction equation

HRID 1623107 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 while still hot 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 while still hot and the yellow filtrate
  4. concentrationwas 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-5a739d221e8b4ce99c03e8e6cca37aa1
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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