Dichloromethane → HCID 10411615, compound

HRID 968942Notes

Reaction equation

HRID 968942 reaction equation
[C:1]([CH:5]([NH:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].C[N:25]1CCO[CH2:27][CH2:26]1.[CH2:31](O)[C:32](N)([CH2:35][OH:36])[CH2:33][OH:34].[CH2:39](Cl)Cl>>[C:1]([CH:5]([N:12]([C:33](=[O:34])[C:32]1[CH:31]=[CH:27][CH:26]=[N:25][C:35]=1[O:36][CH3:39])[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 6344Dichloromethane3×HCID 6503Tris(hydroxymethyl)aminomethaneHCID 79724-MethylmorpholineHCID 59016620HCID 59016620, compound

Product 1

HCID 10411615HCID 10411615, compound

Procedure

In a 25 mL vial, 123.1 mg (0.388 mmol) of 4-ethyl-benzoic acid N′-(1-tert-butyl-heptyl)-hydrazide were dissolved in 5 mL CH2Cl2. 3 equivalents of PS-NMM (polystyrene-SO2NH(CH2)3-morpholine, Argonaut Tech.) were added, followed by 3 mL CH2Cl2 to create a stirable suspension. One equivalent of acid chloride was added, and the reaction mixture was stirred overnight. The next day, 2 equivalents of AP-NCO resin (isocyante scavenger, Argonaut Tech.) and 2 equivalents of AP-trisamine (polystyrene-CH2NHCH2CH2NH(CH2CH2NH2)2, Argonaut Tech.) were added with 3 mL CH2Cl2. The mixture was stirred for four hours and the resins were filtered. The reaction was analyzed by TLC, the solvent was removed, and the residue was dried under vacuum. After silica gel column chromatography using a 0–100% ether in hexane gradient, 107.5 mg of 2-methoxy-nicotinic acid N-(1-tert-butyl-heptyl)-N′-(4-ethyl-benzoyl)-hydrazide were isolated.

Workup

  1. stirringThe mixture was stirred for four hours
  2. filtrationthe resins were filtered
  3. customthe solvent was removed
  4. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-3a44a6a7b4564f0695cb818eff939ba1
Source dataset
uspto-grants-2007_12
Patent number
US07304161B2

Reaction notes

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