Pyridine → HCID 39967700, compound

HRID 624159Notes

Reaction equation

HRID 624159 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][NH2:9])=[O:7].[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1.N1C=CC=CC=1>O1CCCC1>[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:9][NH:8][C:6]([C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)=[O:7])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 685154-Bromobenzoyl chlorideHCID 2816101h-pyrrole-2-carbohydrazide

Product 1

HCID 39967700HCID 39967700, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.750 g of 1H-pyrrole-2-carbohydrazide (5.99 mmol) in 50 ml tetrahydrofuran was added 1.315 g 4-bromobenzoyl chloride (5.99 mmol) and 1 ml pyridine (11.99 mmol) at room temperature under nitrogen. After one hour of stirring at room temperature, the desired product precipitated. The precipitate was filtered, washed with minimum dichloromethane and methanol and dried to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.63 (s, 1H), 10.47 (s, 1H), 10.04 (s, 1H), 7.84-7.88 (m, 2H), 7.75 (d, J=8.8, 1H), 7.75 (q, J=4.2, 1H), 6.91-6.95 (m, 2H), 6.33-6.15 (m, 1H).

Workup

  1. customthe desired product precipitated
  2. filtrationThe precipitate was filtered
  3. washwashed with minimum dichloromethane and methanol
  4. customdried

Sources & evidence

ORD record
ord-bdbce85534c24cb79344b1c79d0ee79d
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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