Cyanogen Bromide → HCID 12614474, compound

HRID 1904307Notes

Reaction equation

HRID 1904307 reaction equation
N#[C:2][Br:3].C(=O)([O-])[O-].[K+].[K+].CN(C)C[CH2:13][S:14][C:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[CH:16]=1>C(Cl)(Cl)Cl.CO>[Br:3][CH2:2][CH2:13][S:14][C:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[CH:16]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 12614416HCID 12614416, compound

Product 1

HCID 12614474HCID 12614474, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

To a stirring solution of 0.36 g of cyanogen bromide, 2.28 g of potassium carbonate in 10 ml of chloroform is added dropwise a solution of 1.0 g of 10-[β-(dimethylamino)ethylthio]dibenz[b,f]oxepin, Example 8, in chloroform. After total addition the reaction mixture is refluxed for 2 hours and the solvent removed leaving an oil. The oil is dissolved in 10 ml of methanol and the methanolic solution refluxed for 10 minutes and again concentrated to recover the oil. The oil is chromatographed through a silica gel column with an eluant of ether. The top fraction is collected and concentrated leaving a white solid, mp 106°-107° C. of 10-[β-(bromo)ethylthio]dibenz[b,f]oxepin.

Workup

  1. additionAfter total addition the reaction mixture
  2. temperatureis refluxed for 2 hours
  3. customthe solvent removed
  4. customleaving an oil
  5. temperaturethe methanolic solution refluxed for 10 minutes
  6. concentrationagain concentrated
  7. customto recover the oil
  8. customThe oil is chromatographed through a silica gel column with an eluant of ether
  9. customThe top fraction is collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-08299c55f0cb45d2b29d33fee5a63933
Source dataset
uspto-grants-1989_06
Patent number
US04837227

Reaction notes

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