Isopropanol → HCID 10488693, compound

HRID 1576329Notes

Reaction equation

HRID 1576329 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]#[N:16].C[O-].[Na+].C(O)(C)C>O>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[C:15]([C:11]2[O:10][CH:14]=[CH:13][CH:12]=2)[N:16]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 692452-FuronitrileHCID 729132-AminobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 10488693HCID 10488693, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.4 g. (0.05 mol) of o-aminobenzonitrile, 4.7 g. (0.05 mol) of 2-furonitrile and 5.4 g. (0.1 mol) of sodium methoxide in 150 ml. of isopropanol are refluxed for 48 hours under a nitrogen atmosphere. The reaction mixture is then decomposed with water and the isopropanol is distilled off. 80 ml. of diethyl ether and 80 ml. of water are added and the precipitate is filtered off. The ethereal layer is separated and the ether is distilled off. The residue is identical to the solid already filtered off. The product is crystallized from a mixture of ethanol and petroleum ether (boiling range 40°-60°C.) to give 4-amino2-(2-furyl)quinazoline, m.p. 219°-221°C. The base is converted into the monohydrochloride, and the salt after crystallization from ethanol melts above 300°C.

Workup

  1. distillationthe isopropanol is distilled off
  2. additionof water are added
  3. filtrationthe precipitate is filtered off
  4. customThe ethereal layer is separated
  5. distillationthe ether is distilled off
  6. filtrationalready filtered off
  7. customThe product is crystallized from a mixture of ethanol and petroleum ether (boiling range 40°-60°C.)

Sources & evidence

ORD record
ord-58e4db50f9264befb61579c71ae17b6a
Source dataset
uspto-grants-1976_09
Patent number
US03980650

Reaction notes

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