Bromobenzene → HCID 21511956, compound

HRID 1576326Notes

Reaction equation

HRID 1576326 reaction equation
[Li].BrC1C=CC=CC=1.[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].[CH3:18][N:19]([CH3:22])[C:20]#[N:21]>O.C(OCC)C>[NH2:13][C:12]1[C:11]2[C:10](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=[C:20]([N:19]([CH3:22])[CH3:18])[N:21]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 15112DimethylcyanamideHCID 729132-AminobenzonitrileHCID 3028194Lithium

Product 1

HCID 21511956HCID 21511956, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Under a nitrogen atmosphere 0.7 g. (0.10 g. at.) of lithium and 7.85 g. (0.05 mol) of bromobenzene are dissolved in 60 ml. of anhydrous diethyl ether. Over the course of about 20 minutes this solution is added to a solution of 5.9 g. of o-aminobenzonitrile in 60 ml. of anhydrous diethyl ether. After 10 minutes, 3.5 g. of dimethylcyanamide, dissolved in 20 ml. of anhydrous diethyl ether, are added and the reaction mixture is refluxed under the nitrogen atmosphere for 6 hours. The next day the mixture is decomposed by addition of water and the precipitate is filtered off. The product is crystallized from a mixture of ethanol and petroleum ether (boiling range 28°-40°C.). 6 g. of 4-amino-2-dimethylaminoquinazoline, m.p. 141°-142°C., are obtained.

Workup

  1. additionOver the course of about 20 minutes this solution is added to a solution of 5.9 g
  2. temperaturethe reaction mixture is refluxed under the nitrogen atmosphere for 6 hours
  3. filtrationthe precipitate is filtered off
  4. customThe product is crystallized from a mixture of ethanol and petroleum ether (boiling range 28°-40°C.)

Sources & evidence

ORD record
ord-d8c2653928644a909d1f075b9fbaafc9
Source dataset
uspto-grants-1976_09
Patent number
US03980650

Reaction notes

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