Bromine → HCID 66958607, compound

HRID 2283764Notes

Reaction equation

HRID 2283764 reaction equation
C([O-])(=O)C.[K+].[CH2:6]([N:8]1[C:12]([CH2:13][CH2:14][N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])=[CH:11][C:10]([C:26]#[N:27])=[N:9]1)[CH3:7].[Br:28]Br.S([O-])(O)=O.[Na+]>C(O)(=O)C.ClCCl>[Br:28][C:11]1[C:10]([C:26]#[N:27])=[N:9][N:8]([CH2:6][CH3:7])[C:12]=1[CH2:13][CH2:14][N:15]1[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]2[C:19]1=[O:20]

Participants

7

Reactant 4

HCID 24408BromineHCID 517044Potassium AcetateHCID 23665763Sodium BisulfiteHCID 66958824HCID 66958824, compound

Product 1

HCID 66958607HCID 66958607, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Potassium acetate (3.9 g, 39.5 mmol) was added to a solution of 1-ethyl-5-(2-phthalimidoethyl)-1H-pyrazole-3-carbonitrile (7.73 g, 26.3 mmol) in acetic acid (37.5 mL) and dichloromethane (75 mL). Bromine (5.88 g, 36.8 mmol) was added, and the reaction was stirred for 14 hours. A precipitate was present. Saturated aqueous sodium hydrogensulfite was added, and the dichloromethane was removed under reduced pressure. Water (500 mL) was added with stirring, and the resulting solid was isolated by filtration, washed with water, and dried on the filter funnel to provide 4-bromo-1-ethyl-5-(2-phthalimidoethyl)-1H-pyrazole-3-carbonitrile.

Workup

  1. customthe dichloromethane was removed under reduced pressure
  2. additionWater (500 mL) was added
  3. stirringwith stirring
  4. customthe resulting solid was isolated by filtration
  5. washwashed with water
  6. customdried on the filter funnel

Sources & evidence

ORD record
ord-8d69ca28261442bca3ad168a0a2d4825
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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