Dimethylformamide → HCID 178419819, compound

HRID 485418Notes

Reaction equation

HRID 485418 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:17]=1)#[N:2].[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+].CN(C=O)C>C(=O)([O-])[O-].[Na+].[Na+]>[NH:18]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]3[CH:12]=[CH:11][C:10]4[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=4[S:8][C:7]=3[CH:17]=2)=[N:2][N:20]=[N:19]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13490383HCID 13490383, compound

Product 1

HCID 178419819HCID 178419819, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A mixture consisting of 4 g. 3-cyanodibenzo[b,f]thiepin (17 millimoles); 1.8 g. sodium azide (28 millimoles); 1.63 g. ammonium chloride (30.5 millimoles) and 50 cc. DMF is refluxed for 17 hours. The mixture is cooled and diluted with aqueous sodium carbonate solution. The solution is extracted with ether, then acidified with aqueous HCl solution. The tetrazole precipitates and is filtered. Crystallization from methanol affords 3.93 g. (83%) yellow product, m.p., 213° C.-214° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionThe solution is extracted with ether
  3. customThe tetrazole precipitates
  4. filtrationis filtered
  5. customCrystallization from methanol
  6. customaffords 3.93 g

Sources & evidence

ORD record
ord-f415a7e830374d7788b0df7ac6ae9654
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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