Hexane → HCID 14476074, compound

HRID 1904310Notes

Reaction equation

HRID 1904310 reaction equation
N#[C:2][Br:3].C(=O)([O-])[O-].[K+].[K+].[F:10][C:11]1[CH:31]=[CH:30][C:14]2[O:15][C:16]3[CH:29]=[CH:28][CH:27]=[CH:26][C:17]=3[CH2:18][CH:19]([S:20][CH2:21]CN(C)C)[C:13]=2[CH:12]=1.CCCCCC>C(Cl)(Cl)Cl>[Br:3][CH2:2][CH2:21][S:20][CH:19]1[CH2:18][C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[O:15][C:14]2[CH:30]=[CH:31][C:11]([F:10])=[CH:12][C:13]1=2

Participants

6

Reactant 4

HCID 8058HexaneHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 14476073HCID 14476073, compound

Product 1

HCID 14476074HCID 14476074, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 2.3 g of cyanogen bromide and 5.0 g of potassium carbonate in 40 ml of chloroform is added portionwise over a 50 minutes span a solution of 4.8 of 2-fluoro-10,11-dihydro-11-[β-(dimethylamino)ethylthio]dibenz[b,f]oxepin, free base of Example 32, in 85 ml of chloroform. After total addition, the mixture is stirred for 20 minutes before being filtered. The filtrate is evaporated to leave an oil which is treated with three portions of boiling hexane. The combined hexane portions are evaporated leaving an oil which is chromatographed through a silica gel column with an eluant of methylene chloride and is recrystallized from cold hexane to give a white powder, mp 46°-48° C. of 11-[β-(bromo)ethylthio]-2-fluoro-10,11-dihydrodibenz[b,f]oxepin.

Workup

  1. additionis added portionwise over a 50 minutes
  2. additionAfter total addition
  3. filtrationbefore being filtered
  4. customThe filtrate is evaporated
  5. customto leave an oil which
  6. customThe combined hexane portions are evaporated
  7. customleaving an oil which
  8. customis chromatographed through a silica gel column with an eluant of methylene chloride
  9. customis recrystallized from cold hexane

Sources & evidence

ORD record
ord-81dfa21c833b4a0584e6dc95ba9b4359
Source dataset
uspto-grants-1989_06
Patent number
US04837227

Reaction notes

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