Dimethylformamide → HCID 178518115, compound

HRID 367219Notes

Reaction equation

HRID 367219 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:20][C:21]#[N:22])[C:9]2[S:10][C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)=[CH:4][CH:3]=1.CN(C=O)C.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:9]2[S:10][C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[CH2:20][C:21]2[NH:30][N:29]=[N:28][N:22]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23287612HCID 23287612, compound

Product 1

HCID 178518115HCID 178518115, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 74 mg (0.23 mmol) of 2-[N-(4-chlorophenyl)-N-(4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-2-yl]amino]acetonitrile and 1 ml of DMF was put in a 20 ml flask. To the mixture were then added 146 mg of sodium azide and 120 mg of ammonium chloride with stirring. The mixture was then stirred at a temperature of 120° C. for 4 hours. The resulting reaction mixture was allowed to cool, poured into water, and then extracted with ethyl acetate. The resulting organic phase was separated, washed with water and saturated brine, and then dried over sodium sulfate. The drying agent was then removed by filtration. The filtrate was then concentrated under reduced pressure. The resulting residue was then washed with cold ethanol to obtain 30 mg of 2-[N-(4-chlorophenyl)-N-(1H-tetrazol-5-ylmethyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customwas put in a 20 ml flask
  2. stirringThe mixture was then stirred at a temperature of 120° C. for 4 hours
  3. customThe resulting reaction mixture
  4. temperatureto cool
  5. extractionextracted with ethyl acetate
  6. customThe resulting organic phase was separated
  7. washwashed with water and saturated brine
  8. dry with materialdried over sodium sulfate
  9. customThe drying agent was then removed by filtration
  10. concentrationThe filtrate was then concentrated under reduced pressure
  11. washThe resulting residue was then washed with cold ethanol

Sources & evidence

ORD record
ord-33b1433787be464ea916c580e2da32b5
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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