Triethylamine → N'-(cyclopropanecarbonyl)-3-iodo-4-methylbenzohydrazide

HRID 1619147

Reaction equation

HRID 1619147 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[I:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([NH:13][NH2:14])=[O:12].C(N(CC)CC)C>ClCCl>[CH:1]1([C:4]([NH:14][NH:13][C:11](=[O:12])[C:10]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:8]([I:7])[CH:9]=2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 597325003-Iodo-4-methylbenzohydrazide

Product 1

HCID 965865N'-(cyclopropanecarbonyl)-3-iodo-4-methylbenzohydrazideYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyclopropanecarbonyl chloride (1.81 mL, 20.0 mmol) in dichloromethane (20 mL) was added dropwise to a stirred solution of 3-iodo-4-methylbenzohydrazide (preparation 55b, 5.00 g, 18.1 mmol) and triethylamine (2.78 mL, 20.0 mmol) in dichloromethane (80 mL) at 0° C. After 2 hours stirring at ambient temperature, the mixture was concentrated in vacuo and water was added to the residue. The resultant precipitate was filtered and was washed with water and diethyl ether to give the title compound (4.75 g, 76%) as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo and water
  2. additionwas added to the residue
  3. filtrationThe resultant precipitate was filtered
  4. washwas washed with water and diethyl ether

Sources & evidence

ORD record
ord-858db07679aa403c948126bf8853f46d
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Linked notes

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