Acetonitrile → HCID 21912953, compound

HRID 1008079Notes

Reaction equation

HRID 1008079 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[C:5]([CH3:18])=[C:4]([CH3:19])[N:3]=1.O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[N-:31]=[N+:32]=[N-:33].[Na+].C(#N)C>O>[CH3:19][C:4]1[N:3]2[N:31]=[N:32][N:33]=[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[C:5]=1[CH3:18]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 33557Sodium AzideHCID 21585214Cerium trichloride heptahydrateHCID 21913098HCID 21913098, compound2×

Product 1

HCID 21912953HCID 21912953, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The preparation of 5-(2-chloro-5,6-dimethyl-3-nitropyridin-4-ylamino)pentan-1-ol was described in Part A of Example 85. Under a nitrogen atmosphere, cerium (III) chloride heptahydrate (8.08 g, 21.7 mmol) and sodium azide (5.64 g, 86.8 mmol) were added to a solution of 5-(2-chloro-5,6-dimethyl-3-nitropyridin-4-ylamino)pentan-1-ol (12.48 g, 43.38 mmol) in a 9:1 mixture of acetonitrile and water (145 mL). The reaction was stirred and heated at reflux for two days then allowed to cool to room temperature. A precipitate was removed by filtration and washed with acetonitrile. The filtrate was concentrated under reduced pressure to provide 12.13 g of 5-[(5,6-dimethyl-8-nitrotetrazolo[1,5-a]pyridin-7-yl)amino]pentan-1-ol as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for two days
  3. customA precipitate was removed by filtration
  4. washwashed with acetonitrile
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c8a97a0730a4301b3488291d21202c1
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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