O-Toluidine → 8-methoxy-2-N,4-N-bis(2-methylphenyl)quinazoline-2,4-diamine

HRID 973568Notes

Reaction equation

HRID 973568 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10](Cl)[N:9]=[C:8]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].[NH2:22][C:23]1[C:24]([CH3:29])=[CH:25][CH:26]=[CH:27][CH:28]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])[N:9]=[C:8]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 10086136HCID 10086136, compound

Product 1

HCID 102485958-methoxy-2-N,4-N-bis(2-methylphenyl)quinazoline-2,4-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-methoxy-4-(2-methylphenylamino)-2-chloroquinazoline (1.00 g, 0.0033 mol) was dissolved in ethanol (15 ml) with o-toluidine (1.06 g, 0.0099 mol) and heated in a sealed vessel at 150° for 5 hours. After cooling and removal of excess solvent in vacuo the solid was chromatographed (silica gel, chloroform). 8-Methoxy-2,4-bis(2-methylphenylamino)quinazoline was isolated as crystals (0.93 g, from ethanol/water, m.p. 185°-187°.

Workup

  1. temperatureheated in a sealed vessel at 150° for 5 hours
  2. temperatureAfter cooling
  3. customremoval of excess solvent in vacuo the solid
  4. customwas chromatographed (silica gel, chloroform)

Sources & evidence

ORD record
ord-843277ef42184f12b3d9ead81ccd94dd
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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