Sodium ethoxide → HCID 22478414, compound

HRID 2184680Notes

Reaction equation

HRID 2184680 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1.[Na].[SH:22][C:23]1[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=1.SC1N(C)C=CN=1.[O-]CC.[Na+]>C(O)C>[CH3:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[NH:13][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][S:22][C:23]3[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=3)[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 224784026-Bromomethyl-4-(3-methylanilino)quinazolineHCID 178480602HCID 178480602, compoundHCID 178480605HCID 178480605, compound

Product 1

HCID 22478414HCID 22478414, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using an analogous procedure to that described in Example 34, 6-bromomethyl-4-(3-methylanilino)quinazoline was reacted with 2-mercapto-1-methylimidazole sodium salt [prepared by the reaction of 2-mercapto-1-methylimidazole and sodium ethoxide in ethanol] to give 4-(3-methylanilino)-6-(N-methylimidazol-2-ylthiomethyl)quinazoline in 65% yield, m.p. 137-139° C.; NMR Spectrum: 2.42 (s, 3H), 3.6 (s, 3H), 4.48 (s, 2H), 6.97 (d, 1H), 7.13 (d, 1H), 7.39 (t, 1H), 7.55 (m, 2H), 7.6 (d, 1H), 7.83 (d, 1H), 7.93 (m, 1H), 8.5 (s, 1H), 8.83 (s, 1H), 10.9 (broad s, 1H); Elemental Analysis: Found C, 48.3; H, 3.6; N, 11.6; C20H19N5S 2CF3CO2H 0.5H2O requires C, 48.1; H, 3.5; N, 11.7%.

Sources & evidence

ORD record
ord-2499979278c74a988342ad334b795290
Source dataset
uspto-grants-2002_06
Patent number
US06399602B1

Reaction notes

Loading…