Hydrochloric Acid → 8-Chloro-3-cyanodibenzo[b,f]thiepin

HRID 485444Notes

Reaction equation

HRID 485444 reaction equation
N[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:11]3[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:12]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[ClH:19].N([O-])=O.[Na+]>O>[Cl:19][C:2]1[CH:7]=[CH:8][C:9]2[S:10][C:11]3[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:12]=3[CH:6]=[CH:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 202702418-Amino-3-cyanodibenzothiepinHCID 23668193Sodium Nitrite

Product 1

HCID 131518898-Chloro-3-cyanodibenzo[b,f]thiepin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

1 G. 8-amino-3-cyanodibenzothiepin is suspended in 16 cc. concentrated hydrochloric acid and 5 cc. of water. The suspension is maintained at a temperature between 0° and 5° C. and 300 mg. sodium nitrite in 2 cc. of cold water is added slowly. The reaction mixture is stirred for 1/2 hour. A mixture of 400 mg. cuprous chloride and 700 mg. cupric chloride dihydrate is then added slowly. After the evolution of nitrogen has subsided, the reaction mixture is stirred at room temperature for 20 minutes, water added and the reaction mixture extracted with chloroform, dried over sodium sulfate and evaporated to dryness to yield 995 mg. (92%) of the pure chloro derivative, m.p. 207°-210° C.

Workup

  1. temperatureThe suspension is maintained at a temperature between 0° and 5° C. and 300 mg
  2. additionA mixture of 400 mg
  3. stirringthe reaction mixture is stirred at room temperature for 20 minutes
  4. extractionthe reaction mixture extracted with chloroform
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customto yield 995 mg

Sources & evidence

ORD record
ord-8386a92cee5a438394a318e408484b0b
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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