Dimethylformamide → HCID 178515101, compound

HRID 367218Notes

Reaction equation

HRID 367218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:14]([CH2:15][C:16]#[N:17])[C:13](=[O:18])[C:12]3[CH:19]=[CH:20][CH:21]=[N:22][C:11]=3[S:10]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[N:14]([CH2:15][C:16]3[NH:30][N:29]=[N:28][N:17]=3)[C:13](=[O:18])[C:12]3[CH:19]=[CH:20][CH:21]=[N:22][C:11]=3[S:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23287655HCID 23287655, compound

Product 1

HCID 178515101HCID 178515101, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 658 mg (2 mmol) of [2-[(4-chlorophenyl)imino]-2,3-dihydro-4-oxo-4H-pyrido[3,2-e]-1,3-thiazin-3-yl]acetonitrile and 8 ml of DMF was put in a 50 ml flask. To the mixture were then added 1.30 g of sodium azide and 1.07 g 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 512 mg of 2,3-dihydro-[2-((4-chlorophenyl)imino]-3-(1H-tetrazol-5-ylmethyl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customwas put in a 50 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-caa73182dcfa4519a57b0268be94c52a
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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