Carbonic acid-guanidine (1:1) → 2,4-Diamino-5-methyl-6-nitroquinazoline

HRID 363768Notes

Reaction equation

HRID 363768 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([CH3:13])[C:3]=1[C:4]#[N:5].C(=O)(O)O.[NH2:18][C:19]([NH2:21])=[NH:20]>C(OCCO)C>[NH2:20][C:19]1[N:21]=[C:4]([NH2:5])[C:3]2[C:2](=[CH:9][CH:8]=[C:7]([N+:10]([O-:12])=[O:11])[C:6]=2[CH3:13])[N:18]=1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 129530402-Chloro-6-methyl-5-nitrobenzonitrile

Product 1

HCID 151523562,4-Diamino-5-methyl-6-nitroquinazolineYield 82.7%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution 29.5 grams (0.150 mole) of 2-chloro-6-methyl-5-nitrobenzonitrile and 54.0 grams (0.300 mole) of guanidine carbonate in 1500 mL of 2-ethoxyethanol was heated at reflux during a 3.5 hour period. After this time, the reaction mixture was concentrated under reduced pressure to a residue. The residue was stirred with 300 mL of water, and the resultant solid was collected by filtration. The solid was washed with 50 mL of water and dried under reduced pressure, yielding 27.2 grams of 2,4-diamino-5-methyl-6-nitroquinazoline. The NMR spectrum was consistent with the proposed structure. The reaction was repeated again.

Workup

  1. temperatureat reflux during a 3.5 hour period
  2. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure to a residue
  3. filtrationthe resultant solid was collected by filtration
  4. washThe solid was washed with 50 mL of water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-41ba2f5160c74aa4a364e523416cb540
Source dataset
uspto-grants-1999_02
Patent number
US05874579

Reaction notes

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