Hydrochloric Acid → HCID 22763456, compound

HRID 1679675Notes

Reaction equation

HRID 1679675 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#B.[ClH:21].[OH-].[Na+]>O1CCCC1>[ClH:21].[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 14798Sodium HydroxideHCID 6328200DiboronHCID 22763500HCID 22763500, compound

Product 1

HCID 22763456HCID 22763456, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Treat 1.4 g. of 5-bromo-2-cyano-3-phenylbenzo[b]thiophene (0.0045 mole) in 40 ml. of tetrahydrofuran with 10 ml. of 1 molar diborane 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 obtain 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
  10. customDry the precipitate

Sources & evidence

ORD record
ord-e8a962f01438487f8e4e759c16250fd1
Source dataset
uspto-grants-1978_03
Patent number
US04081549

Reaction notes

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