Ethylenediamine → Benzo[b]thiophene-6-carbonitrile

HRID 911342Notes

Reaction equation

HRID 911342 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH:13]=1.C(N)CN>CCOCC>[S:10]1[CH:11]=[CH:12][C:8]2[CH:7]=[CH:6][C:5]([C:2]#[N:3])=[CH:13][C:9]1=2

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 127444006-Bromo-benzo[b]thiopheneHCID 178418546HCID 178418546, compound

Product 1

HCID 21816574Benzo[b]thiophene-6-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Heat copper(I) cyanide (0.84 g, 9.4 mmol) and 6-bromobenzo[b]thiophene (prepared as described in WO 01/23381) (1.0 g, 4.7 mmol) at 160° C. for 13 h. Cool the mixture to 0° C., add 33% aqueous ethylenediamine (20 mL) and dilute with ether. Wash the organic mixture with brine, dry over Na2SO4 and evaporate. Purify by chromatography on silica gel eluting with EtOAc/hexane (0:1 to 1:3) to give the desired intermediate (0.58 g, 78%). GC-MS m/z: 159 (M+).

Workup

  1. washWash the organic mixture with brine
  2. dry with materialdry over Na2SO4
  3. customevaporate
  4. customPurify by chromatography on silica gel eluting with EtOAc/hexane (0:1 to 1:3)

Sources & evidence

ORD record
ord-4a96621390c249b5a0be2badce3a7c69
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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