Hydrochloric Acid → HCID 22763456, compound

HRID 1112300Notes

Reaction equation

HRID 1112300 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]([C:15]#[N:16])=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:4]=2[CH:3]=1.B.[ClH:20].[OH-].[Na+]>O1CCCC1>[ClH:20].[NH2:16][CH2:15][C:7]1[S:6][C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][C:4]=2[C:8]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 22763500HCID 22763500, compound

Product 1

HCID 22763456HCID 22763456, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Treat 1.4 g. 5-bromo-2-cyano-3-phenylbenzo[b]thiophene (0.0045 mole) in 40 ml of tetrahydrofuran, with 10 ml of 1 molar borane in tetrahydrofuran. Reflux the solution for 11/2 hours. Slowly add 10 ml of 5% hydrochloric acid. Heat the mixture for 1/2 hour, cool and add sufficient sodium hydroxide solution to basicity. Extract the solution with ether and wash twice with water. Dry the ether layer (MgSO4), filter and mix with 50 ml of ether saturated with hydrogen chloride. Dry the precipitate to yield the title compound; m.p. over 225° (decomp).

Workup

  1. additionTreat 1.4 g
  2. temperatureReflux the solution for 11/2 hours
  3. temperatureHeat the mixture for 1/2 hour
  4. temperaturecool
  5. extractionExtract the solution with ether
  6. washwash twice with water
  7. dry with materialDry the ether layer (MgSO4)
  8. filtrationfilter
  9. additionmix with 50 ml of ether saturated with hydrogen chloride
  10. customDry the precipitate

Sources & evidence

ORD record
ord-9aa481dd3fe14bd083102c0823786d9e
Source dataset
uspto-grants-1978_10
Patent number
US04122034

Reaction notes

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