Sodium Iodide → N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamide

HRID 1958882Notes

Reaction equation

HRID 1958882 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:10]=[CH:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[N:7]=1)=[O:4].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Cl:18][C:13]1[CH:12]=[C:11]([N:8]2[CH:9]=[CH:10][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:7]2)[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 577054132-chloro-N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)acetamide

Product 1

HCID 24743570N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamideYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)acetamide (0.22 g, 0.74 mmol), morpholine (71 mg, 0.81 mmol), potassium carbonate (0.22 g, 1.62 mmol) and sodium iodide (0.11 g, 0.74 mmol) in dry dimethylformamide (5 ml) was stirred and warmed at 100° C., overnight, in a dry nitrogen atmosphere. The solvent was evaporated in vacuo and water was added to the crude residue. The dark solid precipitated was filtered and dried yielding a crude product purified by crystallization in ethyl acetate, and 0.23 g of N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamide was obtained as a beige colour solid with m.p.=125-127° C.

Workup

  1. customThe solvent was evaporated in vacuo and water
  2. additionwas added to the crude residue
  3. customThe dark solid precipitated
  4. filtrationwas filtered
  5. customdried
  6. customyielding a crude product
  7. custompurified by crystallization in ethyl acetate

Sources & evidence

ORD record
ord-52f897bef7384d609ac7015eafa40d33
Source dataset
uspto-grants-2013_04
Patent number
US08410159B2

Reaction notes

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