N,N-Diethyl-p-phenylenediamine → HCID 11964789, compound

HRID 2366443Notes

Reaction equation

HRID 2366443 reaction equation
[C:1](/[C:3](/[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)=[CH:4]\[C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]([O-])=[O:21])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1)#[N:2].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[CH2:52]([N:54]([CH2:62][CH3:63])[C:55]1[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][CH:56]=1)[CH3:53]>C(Cl)Cl>[CH2:62]([N:54]([CH2:52][CH3:53])[C:55]1[CH:60]=[CH:59][C:58]([NH:61][C:20](=[O:21])[CH2:19][CH2:18][C:17]([O:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8]3[S:9][C:5](/[CH:4]=[C:3](\[C:1]#[N:2])/[C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=4)=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)=[O:23])=[CH:57][CH:56]=1)[CH3:63]

Participants

6

Reactant 4

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 79724-Methylmorpholine2×HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 86634875HCID 86634875, compound

Product 1

HCID 11964789HCID 11964789, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 18 (500 mg) was dissolved in methylene chloride (10 mL), and 2-chloro-4,6-dimethoxy-1,3,5-triazine (224 mg) and N-methylmorpholine (129 μL) were added to the solution, followed by stirring with ice cooling for 30 minutes. Subsequently, N,N-diethyl-1,4-phenylenediamine (209 μL) and N methylmorpholine (215 μL) were added to the mixture, followed by stirring at room temperature for 17 hours. The solvent was evaporated to dryness, and the residue was purified by silica gel column chromatography (CHCl3-MeOH), to thereby yield the target product (yield: 322 mg, 49%).

Workup

  1. stirringby stirring at room temperature for 17 hours
  2. customThe solvent was evaporated to dryness
  3. customthe residue was purified by silica gel column chromatography (CHCl3-MeOH)

Sources & evidence

ORD record
ord-86b711c1f903488e8a8d28c476bdb86d
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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