Methane → HCID 21491342, compound

HRID 1973354Notes

Reaction equation

HRID 1973354 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[N:3]=1.[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.C>CN(C)C=O>[ClH:1].[ClH:1].[Cl:19][C:14]1[CH:13]=[C:12]([C:4]2[N:3]=[C:2]([NH:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

5

Reactant 3

HCID 297MethaneHCID 316701-PyrrolidinepropanamineHCID 214913484-Chloro-2-(3,4-dichlorophenyl)quinazoline

Product 1

HCID 21491342HCID 21491342, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-2-(3,4-dichlorophenyl)quinazoline (37.0 g., 0.12 mole) in dimethylformamide (400.0 ml) was added N-(3-aminopropyl) pyrrolidine (31.0 g., 0.24 mole). After stirring and heating the mixture for 4.0 hrs., the mixture was treated with charcoal and filtered. The solution was treated with H2O and then refrigerated. The cream colored powder removed by filtration was suspended in ethereal hydrochloric acid and treated with ethanol. After cooling, the off-white powder was removed by filtration and weighed 57.0 g., (100%). Two recrystallizations from ethanol + HCl/CH3OH + HCl/Charcoal (precipitated with ether) provided an analytical sample melting at 261°-263°. Anal. Calcd. for C21H22Cl2N4.2HCl: C, 53.18; H, 5.10; N, 11.81. Found: C, 52.96; H, 5.19; N, 11.67.

Workup

  1. temperatureheating the mixture for 4.0 hrs
  2. filtrationfiltered
  3. additionThe solution was treated with H2O
  4. customremoved by filtration
  5. additiontreated with ethanol
  6. temperatureAfter cooling
  7. customthe off-white powder was removed by filtration
  8. customTwo recrystallizations from ethanol + HCl/CH3OH + HCl/Charcoal (precipitated with ether)
  9. customprovided an analytical sample melting at 261°-263°

Sources & evidence

ORD record
ord-ac5b5594ca4044fda485ee52e37b4e4e
Source dataset
uspto-grants-1976_12
Patent number
US03997538

Reaction notes

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