Urea → 3-Cyano-8-fluorodibenzo[b,f]thiepine

HRID 485467Notes

Reaction equation

HRID 485467 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1.[H+].[B-](F)(F)(F)[F:21].N([O-])=O.[Na+].NC(N)=O>O>[C:16]([C:13]1[CH:14]=[CH:15][C:9]2[CH:8]=[CH:7][C:6]3[CH:18]=[C:2]([F:21])[CH:3]=[CH:4][C:5]=3[S:11][C:10]=2[CH:12]=1)#[N:17]

Participants

6

Reactant 4

HCID 1176UreaHCID 28118Tetrafluoroboric acidHCID 131518838-Amino-3-cyanodibenzo[b,f]thiepinHCID 23668193Sodium Nitrite

Product 1

HCID 134903873-Cyano-8-fluorodibenzo[b,f]thiepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Suspend 6 gm. of the 3-cyano-8-aminodibenzo[b,f]thiepine from Example 18, Step 1, in 15 ml. of 50% fluoboric acid (HBF4) and 15 ml. of water. Cool the mixture to 3°-5° C. and slowly add 18 ml. of 10% sodium nitrite. Stir in the cold for 4 hours and add urea to destroy the excess sodium nitrite. Separate the solids by filtration and wash with cold 5% fluoboric acid followed by cold water and then ether. Air dry. Suspend the diazonium fluoroborate in 300 ml. of xylene and reflux for 2 hours with stirring. Filter and evaporate the filtrate to dryness. Triturate with ether to obtain the title product (m.p., 146°-148° C.).

Workup

  1. temperatureCool the mixture to 3°-5° C.
  2. customto destroy the excess sodium nitrite
  3. customSeparate the solids
  4. filtrationby filtration
  5. washwash with cold 5% fluoboric acid
  6. customAir dry
  7. temperatureof xylene and reflux for 2 hours
  8. stirringwith stirring
  9. filtrationFilter
  10. customevaporate the filtrate to dryness
  11. customTriturate with ether

Sources & evidence

ORD record
ord-2c6b36c3bda143b8ba8a2e7f27ec5284
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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