Dimethylformamide → HCID 178419819, compound

HRID 1074981Notes

Reaction equation

HRID 1074981 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 fefluxed 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
  7. customm.p., 213° C.-214° C.

Sources & evidence

ORD record
ord-7fc92106765442cb974bb94a0a761bb2
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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