Isopropanol → HCID 178462036, compound

HRID 865656Notes

Reaction equation

HRID 865656 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[N:16][C:17]#[N:18])OC2C=CC=CC=2)[CH:2]=1.[CH3:19][C@@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(C)C>CO>[C:17]([N:16]=[C:8]([NH:27][C@@H:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:19])[NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6431891-Phenethylamine, (+)-HCID 178512277HCID 178512277, compound

Product 1

HCID 178462036HCID 178462036, compoundYield 7,403.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of N-(3-pyridyl)-N'-cyano-O-phenylisourea (see, Example 5 for procedure) (8.00 g, 0.336 mmol), (R)-α-methylbenzylamine (10.8 mL, 0.0835 mol) and isopropanol (53.3 mL) was refluxed, under nitrogen, for 4 hours. The reaction was complete by TLC with 10% MeOH-1% NH4OH-CHCl3. The mixture was concentrated in vacuo. The residue was mixed with EtOAc several times with concentration after each addition; the resulting solid was triturated with hot EtOAc, collected by filtration and recrystallized from MeOH-CH2Cl2 -EtOAc to give 6.6 g of product: mp 185°-187° C.

Workup

  1. temperaturewas refluxed, under nitrogen, for 4 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionThe residue was mixed with EtOAc several times with concentration
  4. additionafter each addition
  5. customthe resulting solid was triturated with hot EtOAc
  6. filtrationcollected by filtration
  7. customrecrystallized from MeOH-CH2Cl2 -EtOAc

Sources & evidence

ORD record
ord-234934d9561a4bff87038ff3e23c8572
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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