Pyridine → N-(4-mercaptophenyl)cyclopropanecarboxamide

HRID 1689741Notes

Reaction equation

HRID 1689741 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:15]1([C:18](Cl)=[O:19])[CH2:17][CH2:16]1>CCOC(C)=O>[CH:15]1([C:18]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=2)=[O:19])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 145104-AminothiophenolHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 16722082N-(4-mercaptophenyl)cyclopropanecarboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4-aminothiophenol (9.4 g, 75.0 mmol, 1.5 equiv) and pyridine (8.09 mL, 100.0 mmol, 2 equiv) at 0° C. was added cyclopropanecarbonyl chloride (4.58 mL, 50.0 mmol, 1 equiv) drop wise. The reaction was stirred from 0° C. to room temperature for overnight, diluted with EtOAc (200 mL), washed with 1 N HCl (50 mL×4), dried over Na2SO4, concentrated, and dried under vacuum to yield the compound 5 as a off-white solid (8.5 g, 88%).

Workup

  1. washwashed with 1 N HCl (50 mL×4)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9de31b1000694f7daa52295ae478b804
Source dataset
uspto-grants-2012_04
Patent number
US08153630B2

Reaction notes

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