Ammonium Chloride → 4-[(5-Ethyl-1H-pyrrol-2-yl)carbonyl]benzonitrile

HRID 860405Notes

Reaction equation

HRID 860405 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[CH:6][CH:7]=1)[CH3:2].C[Mg]Br.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:27])SC2C=CC=CN=2)=[CH:15][CH:14]=1)#[N:12].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1>[CH2:1]([C:3]1[NH:4][C:5]([C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:18][CH:17]=2)=[O:27])=[CH:6][CH:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 1370752-EthylpyrroleHCID 12548807S-(2-pyridinyl) 4-cyanobenzenecarbothioateHCID 178418573HCID 178418573, compound

Product 1

HCID 450955294-[(5-Ethyl-1H-pyrrol-2-yl)carbonyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethyl-1H-pyrrole in toluene (120 mL) was added dropwise 1M methylmagnesium bromide in tetrahydrofuran (170 mL) in a dry ice-acetone bath below −60° C. over 30 minutes. Then the mixture was stirred in an ice-water bath for 40 minutes. To this reaction mixture was added S-(2-pyridinyl) 4-cyanobenzenecarbothioate (15.2 g) portionwise over 10 minutes in a dryice-acetone bath. After 1.5 hours stirring, saturated ammonium chloride (100 mL) was added therein and the reaction mixture was allowed to ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1N sodium hydroxide (100 mL) twice, water, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with isopropyl ether to give 4-[(5-ethyl-1H-pyrrol-2-yl)carbonyl]benzonitrile (12.7 g) as a pale yellow solid.

Workup

  1. stirringAfter 1.5 hours stirring
  2. customwas allowed to ambient temperature
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 1N sodium hydroxide (100 mL) twice
  5. dry with materialwater, and brine, dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-fae7f706fe1f4309ac178476214162b1
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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