Sulfuric Acid → 3-Cyano-8-hydroxydibenzo[b,f]thiepine

HRID 485464Notes

Reaction equation

HRID 485464 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.S(=O)(=O)(O)[OH:20].N([O-])=O.[Na+]>O>[C:16]([C:13]1[CH:14]=[CH:15][C:9]2[CH:8]=[CH:7][C:6]3[CH:18]=[C:2]([OH:20])[CH:3]=[CH:4][C:5]=3[S:11][C:10]=2[CH:12]=1)#[N:17]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 131518838-Amino-3-cyanodibenzo[b,f]thiepinHCID 23668193Sodium Nitrite

Product 1

HCID 134903843-Cyano-8-hydroxydibenzo[b,f]thiepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
3 °C

Procedure

Suspend 50 mg. of the 3-cyano-8-aminodibenzo[b,f]thiepine from Example 18, Step 1, in 2 ml. of 10% sulfuric acid and cool to 3° C. Add dropwise 0.2 ml. of 10% aqueous sodium nitrite solution. Stir at 3° C. for 2 hours and allow to warm to 15° C. for 1 hour. Add the solution dropwise to 50 ml. of boiling 10% sulfuric acid and continue heating for 15 minutes. Dilute with cold water and filter. Wash the solids with water and dry to obtain the title product (m.p., 224°-227° C.).

Workup

  1. additionAdd dropwise 0.2 ml
  2. temperatureto warm to 15° C. for 1 hour
  3. additionAdd the solution dropwise to 50 ml
  4. temperaturecontinue heating for 15 minutes
  5. filtrationfilter
  6. washWash the solids with water
  7. customdry

Sources & evidence

ORD record
ord-e957652a380d4f2c8e986232ccc31c51
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

Loading…